Tag: M.W=200-300

Some common heterocyclic compound, 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, molecular formula is C13H16BrNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. HPLC of Formula: C13H16BrNO2

To a 10OmL 3-neck round bottom flask are added 5-bromo-l,3-dihydro-isoindole-2- carboxylic acid tert-butyl ester (13.42 mmol; 1.0 equiv), Pd(OAc)2 (0.34 mmol; 0.025 equiv), and P(o-tol)3 (0.67 mmol; 0.05 equiv) and the flask is evacuated and purged with N2 three times. DMF (34 mL), methyl acrylate (14.76 mmol; 1.1 equiv), and Et3N (67.1 mmol; 5.0 equiv) are added and the reaction mixture is heated to 130 C for 15 h. The reaction is cooled to room temperature, diluted with Et2O (200 mL), and the organic layer is washed with 10% citric acid, saturated sodium hydrogen carbonate, and brine. The combined organic extracts are dried (MgSO4), filtered, and concentrated to afford the crude product, which is then purified by silica gel chromatography to yield 5-(2-methoxycarbonyl-vinyl)-l,3- dihydro-isoindole-2-carboxylic acid tert-butyl ester as a yellow solid (1.7 g; 42% yield). 1H NMR (400 MHz, CD3OD): delta 7.68 (d, J= 16 Hz, 1 H), 7.53 (m, 2 H), 7.32 (t, J= 8.0 Hz, 1 H), 6.52 (d, J= 16 Hz, 1 H), 4.64 (d, J= 8 Hz, 4 H), 3.78 (s, 3 H), 1.52 (s, 9 H). MS m/z 305.0 (M+l)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 201940-08-1, its application will become more common.

Reference:
Patent; NOVARTIS AG; WO2008/76954; (2008); A2;,
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Some common heterocyclic compound, 919103-45-0, name is 6-Iodoindolin-2-one, molecular formula is C8H6INO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Formula: C8H6INO

[0496] A nitrogen purged vessel is loaded with starting material 6-Iodoindolinone (105 kg, 405 mol, 1.0 eq), catalyst 4-dimethylaminopyridine (DMAP) (2.52 kg) under argon counter flow. Then triethylamine (145 kg, 3.5 eq) and solvent 2-methyltetrahydrofuran (605 kg) are charged to the vessel and the resulting solution is cooled to -15 C. to -5 C. (preferentially -10 C.). Benzoylchloride (176.6 kg, 3.1 eq) is added to this mixture at an internal temperature of -10 C. to 50 C. within at least 30 min. [0497] The addition funnel is then flushed with 2-methyltetrahydrofuran (22 kg) and the reaction mixture is stirred for an additional hour at an internal temperature of 10 to 30 C. If the content of starting material 6-iodoindolinone is greater than 2.5 area % (HPLC), another portion of benzoylchloride (5.7 kg) is added to complete the reaction. If the content of starting material 6-iodoindolinone is smaller than 2.5 area % (HPLC), lithium hydroxide (59.4 kg, 6.0 eq) is added in 5 differently sized portions (1st: 18.0 kg, 2nd: 6.0 kg, 3rd: 6.0 kg, 4th: 15.0 kg, 5th: 14.4 kg) in a temperature controlled manner: After the two first portions, the mixture is stirred for 1 hour. After portion 3 and 4, the mixture is stirred for 30 min. After the last portion, the mixture is stirred for two hours. The reaction mixture (suspension) is then stirred for at least 12 hours at an internal temperature of 20 to 30 C. If the content of the non isolated intermediate of formula (V) is smaller than 0.5 area % (HPLC), water (525 L) is added and the mixture is heated to an internal temperature of 60 to 70 C. under stirring. Then the stirrer is switched off, the mixture is settled down and the phases are separated at an internal temperature of 60 to 70 C. To the upper organic layer, water (525 L) is added and a second phase separation is carried out at an internal temperature of 60 to 70 C. (Optionally, the mixture might be left stand at room temperature for up to 24 hours.) Then a partial solvent switch to tetrahydrofuran is carried out: Solvent is distilled off three times at a jacket temperature of 70 C. down to a residual volume of 390 L followed by addition of tetrahydrofuran (1st: 233 kg, 2nd: 233 kg, 3rd: 117 kg). For crystallization, firstly, methanol (83 kg) is added. [0498] Optionally, the mixture might be left stand at room temperature for up to 24 hours. Secondly, water (112 L) is added at an internal temperature of 60 to 70 C., followed by addition of conc. hydrochloric acid (156.2 kg). The addition funnel is flushed with water (20 L). The resulting suspension is cooled to 20 to 30 C. within at least 70 min (optionally, the mixture might be left stand at room temperature for up to 72 hours) and then to an internal temperature of minus 5 to 5 C. within at least 30 min. The suspension is then centrifuged and the solid is washed with water (368 L) followed by methanol (112 kg) and dried at a jacket temperature of 50 C. until <=1% of residual solvent is reached. The enol product of formula (IV) is obtained as solid in 84.6% yield. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 919103-45-0, its application will become more common. Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MAIER, Gerd-Michael; BAUM, Anke; BETZEMEIER, Bodo; HENRY, Manuel; HERTER, Rolf; REISER, Ulrich; SINI, Patrizia; WEBER, Dirk; WERTHMANN, Ulrike; ZAHN, Stephan Karl; US2014/18372; (2014); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 868066-91-5, name is 5-Bromo-2-methylisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H8BrNO

In a vial was combined 5-bromo-2-methylisoindolin-1-one (226 mg, 1.00 mmol) [Ark Pharm cat AK-37748], 4,4,5,5,4?,4?,5?,5?-octamethyl-[2,2?]bi[[1,3,2]dioxaborolanyl] (0.533 g, 2.10 mmol), potassium acetate (294 mg, 3.00 mmol), 1,4-dioxane (5.0 mL), and [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (36.6 mg, 0.050 mmol). The vial was de-gassed by bubbling nitrogen through the solvent for 5 minutes then heated to 90 C. overnight. The mixture was allowed to cool to room temperature and was then filtered using a syringe filter. The filtrate was then concentrated under reduced pressure and used without further purification. LC-MS calculated for C15H21BNO3(M+H)+: m/z=274.2. found 274.1.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 868066-91-5.

Reference:
Patent; Incyte Corporation; Wu, Liangxing; Konkol, Leah C.; Lajkiewicz, Neil; Lu, Liang; Xu, Meizhong; Yao, Wenqing; Yu, Zhiyong; Zhang, Colin; He, Chunhong; (107 pag.)US2016/9712; (2016); A1;,
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Reference of 6941-75-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of LIALH4 (8.8 mL of 1 M solution in Et20, 8.8 mmol) in dry THF (13 mL) was cooled to 0 C. Concentrated H2S04 (0.42 g, 4.3 mmol) was added dropwise, and the resulting mixture was stirred at 0 C for 30 min. 5-Bromo-lH-isoindole-1, 3 (2H)- dione (0.409 g, 1. 81 mmol) was added in portions over 15 minutes, and the reaction was allowed to warm to room temperature when the addition was complete. The reaction was stirred at room temperature for 2. 5H, and then cooled back to 0 C and quenched by the addition OF MEOH (2 mL). Et2O was added (50 mL), followed by NA2S04-10H20. The mixture was stirred vigorously until the organic layer was clear. The mixture was then filtered and concentrated in VACUO. Purification by column chromatography (4: 1 CH2CL2; MeOH + 0. 1% conc. NH3) provided the title compound (0.128 g, 36%). 1H-NMR (CDCl3): No. 7.38 (s 1H), 7.33 (D,@ J=7. 6 Hz, 1H), 7.12 (d, J=8. 0 Hz, 1H), 4.21 (s, 2H), 4.17 (s, 2H), 2.09 (s, 1H). MS (ESI) (M+H) +=198/200.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Bromoisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2004/60882; (2004); A1;,
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Reference of 3416-57-7, These common heterocyclic compound, 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

5.5. Examples 5-13; Similar to Examples 3 and 4,5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ol was prepared using the following solvent/base combinations for the preparation of the 2-amino-4-methyl-1H-pyrrole-3-carboxamide intermediate:

The synthetic route of 3416-57-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bednarz, Mark S.; Kanamarlapudi, Ramanaiah C.; Wu, Wenxue; US2008/97098; (2008); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C9H4F3NO3

General procedure: A mixture of indoline-2,3-dione 1 (1mmol), l-tryptophan (2a) or l-histidine 2b (1mmol) and (E)-(2-nitrovinyl)benzene 3 (1.1mmol) was heated while stirred in [bmim]Br as the reaction medium (3mL) for 1hat 100C. After completion of the reaction (TLC), EtOAc (5mL) was added and the reaction mixture was stirred for 10min. This treatment was repeated and the combined ethyl acetate layers were removed in vacuo. The crude product was purified by recrystallization of the residue from EtOH (compounds 4) or by column chromatography (compounds 5). After extraction of the product, the ionic liquid was dried under vacuum at 80C for 2h to eliminate any water and could be reused for subsequent runs of the reaction.

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Periasamy, Vaiyapuri Subbarayan; Athinarayanan, Jegan; Alshatwi, Ali A.; Govindasami, Periyasami; Altaf, Mohammad; Menendez, J. Carlos; Tetrahedron; vol. 74; 38; (2018); p. 5358 – 5366;,
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Synthetic Route of 129487-92-9,Some common heterocyclic compound, 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, molecular formula is C13H18N2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Part H. To tert-butyl-5-amino-1-indolinecarboxylate (1.90 g, 8.2 mmol) was added 5-bromovaleryl chloride (1.4 mL, 9.0 mmol) and 18 mL of THF. After stirring for 5 min at rt under N2, potassium tert-butoxide (9 mL, 9 mmol; 1.0 M in THF) was added in one portion, and the resulting brown solution was stirred under N2 for 30 min. A second portion of potassium tert-butoxide (9 mL) was added, and the resulting brown suspension was stirred for 15 min. An additional 0.10 mL-portion of 5-bromovaleryl chloride and a 4.5 mL-portion of potassium tert-butoxide were added, and the mixture was stirred for 30 min. The reaction was then poured into H2O (80 mL). The aqueous layer was washed with EtOAc (3*50 mL), and the combined organic layers were washed with brine, dried over Na2SO4, and filtered. The filtrate was concentrated and the resulting residue was purified by radial chromatography (50% EtOAc in hexanes) to afford tert-butyl 5-(2-oxo-1-piperidinyl)-1-indolinecarboxylate as a pink solid (1.30 g, 50%). LRMS (AP+): 317.2 (M+H)+. 1H NMR (CDCl3) delta7.40-7.80 (br m, 1H), 7.01 (s, 1H), 6.97 (d, 1H), 3.94 (t, 2H), 3.55 (br m, 2H), 3.09 (t, 2H), 2.49 (br m, 2H), 1.91 (br m, 4 H), 1.52 (s, 9H).

The synthetic route of 129487-92-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pinto, Donald J.P.; Quan, Mimi L.; Orwat, Michael J.; Li, Yun-Long; Han, Wei; Qiao, Jennifer X.; Lam, Patrick Y.S.; Koch, Stephanie L.; US2003/191115; (2003); A1;,
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Synthetic Route of 5332-26-3, These common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

Statistics shows that 2-(Bromomethyl)isoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 5332-26-3.

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-(Bromomethyl)isoindoline-1,3-dione

General procedure: After the compound 1o (700 mg, 1.68 mmol) was dissolved in dichloromethane (15 mL), potassium hydroxide (278 mg, 4.22 mmol) and tetrabutylammonium bromide (60 mg) were added thereto, and iodomethyl (0.525 mL, 8.435 mmol) was slowly added thereto at room temperature. This solution was stirred for 10 hours at 25C. Cooling water was added to the reaction material, and the result was adjusted to pH 5 to 6 using a 2N aqueous hydrochloric acid solution. After the organic layer was separated and taken, the aqueous layer was extracted once with dichloromethane, and the organic layers were combined, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was separated using silica gel column chromatography (normal-hexane/ethyl acetate=4/1) to give a pure target compound 1z (574 mg, 79%). 1H-NMR (300 MHz, CDCl3) delta 0.97 (s, 9H), 1.49 (s, 3H), 2.28 (s, 3H), 2.71 (s, 3H), 3.65 (s, 3H), 3.75 (s, 3H), 5.07 (s, 1H), 7.24 (m, 1H), 7.43 (m, 3H); MS (EI, m/e)=428 (M+). A target compound 19a (780 mg, 94%) was obtained by reacting the compound 1o (600 mg, 1.446 mmol) inthe same manner as in Step 1 of Example 1, except that N-(bromomethyl)phthalimide (787 mg, 3.0 equivalents) andpotassium hydroxide (400 mg, 5 equivalents) were used instead of iodomethyl and the stirring was carried out for 7hours at 20C. 1H-NMR (300 MHz, CDCl3) delta 0.98 (s, 9H), 1.46 (s, 3H), 2.45 (s, 3H), 2.65 (s, 3H), 3.63 (s, 3H), 5.04 (s, 1H),6.08 (AB-q, 2H), 7.24 (m, 2H), 7.37 (m, 2H), 7.73 (m, 2H), 7.68 (m, 2H); MS (EI, m/e)=573 (M+).

According to the analysis of related databases, 5332-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Korea Research Institute of Chemical Technology; SON, Jong Chan; KIM, Bong Jin; KIM, Jae Hak; LEE, Ill Young; YUN, Chang Soo; LEE, Sang Ho; LEE, Chong Kgo; (98 pag.)EP2781519; (2014); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 264916-06-5, name is tert-Butyl 5-aminoisoindoline-2-carboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C13H18N2O2

(2) 2-tert-Butoxycarbonyl-5-(2-nitrophenylamino)isoindoline A dimethylformamide (10 ml) suspension of 5-amino-2-tert-butoxycarbonylisoindoline (5.3 g, 22.6 mmol), o-fluoronitrobenzene (7.15 ml, 22.6 mmol) and potassium carbonate (3.12 g, 22.6 mmol) was stirred at 145 C. for 2 hours under nitrogen atmosphere. After cooling, the reaction mixture was diluted with ethyl acetate and washed with water. After drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography to give 2-tert-butoxycarbonyl-5-(2-nitrophenylamino)isoindoline (4.9 g, 61%) as an oil. 1H-NMR(CDCl3) delta: 1.53(9H, s), 4.67(2H, s), 4.70(2H, s), 6.76(1H, t, J=6.8 Hz), 7.15-7.41(5H, m), 8.20(1H, d, J=8.8 Hz), 9.47(1H, bs).

The synthetic route of 264916-06-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Oi, Satoru; Suzuki, Nobuhiro; Matsumoto, Takahiro; US2003/149027; (2003); A1;,
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