Tag: M.W=200-300

Synthetic Route of 423116-18-1, A common heterocyclic compound, 423116-18-1, name is 2-(4-Oxocyclohexylmethyl)isoindole-1,3-dione, molecular formula is C15H15NO3, 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.

Sodium cyanoborohydride (48.5 g, 772 mmol) was added portionwise to a solution of 2-((4-oxocyclohexyl)methyl)isoindoline-1,3-dione (100 g, 389 mmol, Intermediate 34) in AcOH (1.0 L), and the resulting mixture was stirred at rt for 16 h. After this time, the mixture was concentrated, and the concentrate was dissolved in EtOAc. The resulting solution washed twice with a saturated aqueous NaHCO3 solution, dried with anhydrous Na2SO4, filtered, and concentrated to afford the title compound as a colorless solid, which was used in the next step without further purification.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Janssen Pharmaceutica NV; Goldberg, Steven; Martin, Connor L.; Fennema, Elizabeth G.; Wolin, Ronald L.; Fourie, Anne M.; Xue, Xiaohua; (85 pag.)US2019/382350; (2019); 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. 3335-98-6, name is 1-Phenyloxindole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C14H11NO

General procedure: A mixture of oxindoles (2.0102 mmol), cinnamaldehyde,a base and a prescribed amount of TIPS-b-CDwas stirred in solvents(2 mL) at 10 C. After the removal of solvent in vacuo, the residuewas analyzed by 1H NMR to determine the reaction conversion andproduct distributions. The product was isolated by silica gel columnchromatography with a hexane/ethyl acetate (4:1, v/v) eluent. 4.5.12 (E)-N-Phenyl-3-(3′-phenylallylidene)-indolin-2-one ((E)-3g) Yellow prisms: mp 158-159 C, 1H NMR (DMSO-d6) delta 6.79 (d, J=7.7 Hz, 1H), 7.16 (dd, J=7.7, 7.7 Hz, 1H), 7.28 (dd, J=7.7, 7.7 Hz, 1H), 7.40-7.50 (m, 7H), 7.51 (s, 1H), 7.56-7.61 (m, 2H), 7.82-7.89 (m, 3H), 8.17 (d, J=7.7 Hz, 1H). 13C NMR (DMSO-d6) delta 109.0, 121.5, 122.7, 123.2, 124.2, 124.4, 126.9, 127.9, 128.3, 129.0, 129.2, 129.6, 130.0, 134.4, 135.8, 136.2, 142.8, 145.8, 166.9. IR: 1699.82 (C=O). HRMS (EI) m/z calcd for C23H17NO: 323.1310, found 323.1313.

According to the analysis of related databases, 3335-98-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Asahara, Haruyasu; Kida, Toshiyuki; Hinoue, Tomoaki; Akashi, Mitsuru; Tetrahedron; vol. 69; 45; (2013); p. 9428 – 9433;,
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Application of 20870-90-0, The chemical industry reduces the impact on the environment during synthesis 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, I believe this compound will play a more active role in future production and life.

A mixture of 5-bromo-N-methyloxindole(5 g, 22 mmol) and POCl3 (40 mL) was stirred and refluxed for 2h. After cooling, themixture was poured into ice water, and then extracted with dichloromethane (MC) forthree times. The combined organic layers were dried over anhydrous magnesium sulfate,filtered, and concentrated. The solid was washed with MC, white solid NMT (2.6 g) wasprepared. Yield was 61%.1H-NMR (300MHz, THF) delta(ppm) : 8.58 (s, 3H), 7.63-7.60 (d, 3H), 7.57-7.53 (d, 3H),4.40 (s, 9H).

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-Bromo-1-methyl-2-oxoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kang, Hyeonmi; Lee, Hayoon; Shin, Hwangyu; Kang, Seokwoo; Kim, Beomjin; Park, Jongwook; Molecular Crystals and Liquid Crystals; vol. 618; 1; (2015); p. 47 – 54;,
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954-81-4, name is N-(5-Bromopentyl)phthalimide, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C13H14BrNO2

General procedure: To a stirred solution of 2-5 (5 mmol) in THF (60 mL) was added potassium thioacetate (15 mmol), and the mixture was refluxed for 3-4 h. And the solvent was evaporated to dryness in vacuo, and then added water (30 mL), and the organic materials were extracted with EtOAc (3×30 mL). The combined extracts were washed with water and brine, dried over anhydrous MgSO4, and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (EtOAc:petroleum ether=1:8) to give compounds 6-9 as white powder.

The synthetic route of 954-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hu, Kun; Qi, Yan-Jie; Zhao, Juan; Jiang, He-Fei; Chen, Xin; Ren, Jie; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 529 – 539;,
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Related Products of 201940-08-1,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.

A mixture of 5-bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (200 mg, 0.67 mmol), Pd (OAc) 2 (30 mg, 0.2 equiv), DPPP (55 mg, 0.2 equiv), TEA (0.93 mL, 10 equiv) and MeOH : DMSO (1: 1,4 mL) was stirred for 16 h under CO (balloon) at 80 C. LC-MS and TLC (20% EtOAc-Hexane) showed completion of the reaction. The Reaction mixture was concentrated to remove MeOH and diluted with EtOAc (10 mL), and washed with water (2 x 25 mL). The organic layer was dried (Na2S04), concentrated and purified by silica gel column chromatography (eluent = 20% EtOAc-Hexane), giving pure 1, 3-dihydro-isoindole-2,5- dicarboxylic acid 2-tert-butyl ester 5-methyl ester (150 mg, 81 %). MS (APCI+) : m/z 178.1 (MH+-Boc).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 5-bromoisoindoline-2-carboxylate, its application will become more common.

Reference:
Patent; INTERMUNE, INC.; ARRAY BIOPHARMA INC.; WO2005/37214; (2005); A2;,
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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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., SDS of cas: 2058-72-2

To a sol. of 5-bromo-1-methyl-1 H-indole- 2,3-dione (3.60 g, 15.0 mmol) in THF (100 mL) are added sequentially at rt trifluoromethyl)trimethylsilane (4.43 mL, 30.0 mmol) and CsF (91.1 mg, 0.60 mmol). The resulting sol. is stirred at rt overnight. The mixture is quenched with cold water (100 mL). The mixture is extracted with EtOAc (3 x 100 mL). The comb. org. layers are washed with brine (100 mL), dried over MgS04, filtered, and the solvents are removed under reduced pressure. Purification of the residue by automated FC (Combiflash, column 80 g, flow 60 mL/min, EtOAc / heptane 0:100 ? 20:80) yields the tri methyl si lyl -protected product. To a sol. of this isolated compound in MeOH (50 mL) is added aq. 2M HCI (40 mL). The resulting sol. is stirred at rt for 2 h. The reaction is diluted with CH2CI2 (100 mL). The layers are separated and the aq. phase is extracted with CH2CI2 (2x 50 mL). The comb. org. layers are washed with brine (1 x 50 mL), dried over MgS04, filtered, and the solvents are removed under reduced pressure to yield the crude title product. LC-MS: tR = 0.79 min (conditions 3).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; SIEGRIST, Romain; HEIDMANN, Bibia; STAMM, Simon; GATFIELD, John; BEZENCON, Olivier; WO2015/186056; (2015); A1;,
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Related Products of 132898-96-5, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 132898-96-5 as follows.

Example 4 (S)-5-(2-Phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione (10). To a solution of 9 (1.46 g, 5.2 mmol) in CH2Cl2 (5 mL) was added trifluoroacetic acid (5 mL) at 0 C. The mixture was stirred at 0 C. for 15 min. After evaporation of the solvent in vacuo, CH2Cl2 (15 mL) and triethylamine (2 mL) were added, then a solution of 6 (1.44 g, 5.9 mmol) in THF (25 mL) was added at 0 C. The reaction mixture was stirred overnight at room temperature. The solvent was evaporated in vacuo, then ethyl acetate (150 mL) was added, washed with water (50 mL*2) and saturated NaCl (50 mL), and dried over Na2SO4. After evaporation of the ethyl acetate, the crude product was purified with ether to afford 1.7 g (84%) of 10 as a yellow solid, mp 204.5-205.9 C. 1H NMR (300 MHz, CDCl3) delta 8.94 (s, 1H), 7.77 (dd, J=8.25 Hz, J=2.1 Hz, 1H), 7.67 (s, 1H), 7.02 (t, J=8.7 Hz, 2H), 6.84 (d, J=8.1 Hz, 1H), 6.69 (t, J=7.2 Hz, 1H), 6.63 (d, J=7.8 Hz, 2H), 3.89 (m, 1H), 3.75-3.66 (m, 2H), 3.23 (m, 1H), 2.96 (m, 1H), 1.72 (m, 2H), 1.54-1.42 (m, 2H). LRMS (FAB) m/e: 387.1 (M+H, 100). Anal. Calcd for C19.N2O5S: C, 59.06, H, 4.70; N, 7.25. Found: C, 58.99, H, 4.74, N, 7.11.

According to the analysis of related databases, 132898-96-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Washington University in St. Louis; US2009/68105; (2009); A1;,
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Related Products of 2058-72-2, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 2058-72-2 as follows.

General procedure: Dialkyl acetylenedicarboxylate 2 (1 mmol) was added to a magnetically stirred 5 mL flat bottom flask containing hydrazine hydrate (1 mmol) and H2O (2 mL) at room temperature. After 10 min, isatin 1(1 mmol) malononitrile (1 mmol) and NaCl (20 mol %) were added and the reaction heated at 50 C for 10 min. After completion of the reaction (monitoring by TLC), the reaction mixture was filtered and the precipitate washed with water and then ether to afford the pure products 3a-h. Methyl 6?-amino-5-bromo-5?-cyano-1-methyl-2-oxo-1?H-spiro-[indoline-3,4?-pyrano[2,3-c]pyrazole]-3?-carboxylate (3g): Yellow powder; yield: 0.25 (80%); m.p. 275-276 C; IR (KBr): 3432, 3307, 3173 (NH2and 2NH), 2200 (C?N), 1720 (CO2Me), 1698 (NCO), 1638, 1602, 1487 (Ar), 1190 (C-O) cm-1; 1H NMR: delta3.35 (3H, s, NCH3), 3.48 (3H, s, OCH3), 7.09 (1H, d, 3JHH= 7.6 Hz, CH6of Ar), 7.31 (1H, s, CH4of Ar), 7.44 (2H, s, NH2), 7.50 (1H, d, 3JHH= 7.2 Hz, CH7of Ar), 14.05 (1H, s, NH) ; 13C NMR: delta26.5 (NCH3), 47.0 (Cspiro), 52.0 (OCH3), 55.5 (C-CN), 99.8 (C3?), 110.2 (CH7), 114.3 (C-Br), 117.8 (CN), 126.4 (CH4), 128.3 (C3a), 131.3 (CH6), 135.2 (C-CO2Me), 142.9 (C7a), 155.9 (OCN), 157.6 (CO2Me), 161.2 (C-NH2), 175.4 (C=O of isatin); MS (EI, 70 eV): m/z (%) = 430 [M+], 403, 287, 142, 101, 83, 59. Anal. calcd for C17H12BrN5O4(430.21): C, 47.46; H, 2.81; N, 16.28; found: C, 47.39; H, 2.74; N, 16.37%.

According to the analysis of related databases, 2058-72-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Alizadeh, Abdolali; Moafi, Leila; Journal of Chemical Research; vol. 39; 8; (2015); p. 464 – 466;,
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Related Products of 4702-13-0,Some common heterocyclic compound, 4702-13-0, name is N-Phthaloylglycine, molecular formula is C10H7NO4, 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: A mixture of compound [3-7]a-i (0.01mole) and thionyl chloride (0.01mole) placed in dry benzene (10 ml.) and refluxed for 7 hours. The excess of thionyl chloride and benzene were removed under vacuum after cooling .

The synthetic route of 4702-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Samir, Ali H.; Saeed, Ruwaidah S.; Matty, Fadhel S.; Oriental Journal of Chemistry; vol. 34; 1; (2018); p. 286 – 294;,
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Application of 552330-86-6, 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. 552330-86-6, name is 5-Bromoisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 5-bromoisoindolin-1-one (636 mg,3.0 mmol), 1D (800 mg, 3.0 mmol), Pd2(dba)3 (82 mg, 0.09 mmol), Xantphos (52 mg, 0.09 mmol) and Cs2CO3 (1.17 g, 3.6 mmol) in dioxane (60 mE) was heated to 1000 C. for 4 h. After that time, the mixture was allowed to cool to room temperature and filtered. The filtrate was concentrated under vacuum and purified by column chromatography on silica gel (1%-10% EtOAc in pet. ether) to afford 5A (400 mg, 34%) as a yellow solid: ?H NMR (400 MHz, DMSO-d5) oe8.71 (s, 1H), 8.61 (d, J=8.4 Hz, 1H), 8.07 (t, J=8.4 Hz, 1H),8.0 (d, J=7.6 Hz, 1H), 7.89 (d, J=8 Hz, 1H), 7.76 (d, J=3.2 Hz, 2H), 5.17 (s, 2H), 4.11-4.04 (m, 1H), 1.14-1.11 (m, 2H), 1.0-0.95 (m, 2H); ESI mlz 396.1, 398.1 [M+1].

The chemical industry reduces the impact on the environment during synthesis 5-Bromoisoindolin-1-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); A1;,
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