Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 61-70-1, name is 1-Methylindolin-2-one, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 61-70-1, SDS of cas: 61-70-1

No. A1-173: 1-(3-Bromophenyl)-N-(1?-methyl-2?-oxo-1?,2?-dihydrospiro[cyclopropane-1,3?-indol]-5-yl)methanesulfonamide (0127) (0128) Together, 1-methyl-1,3-dihydro-2H-indol-2-one (2.00 g, 14 mmol) and 1,2-dibromoethane (3.83 g, 20 mmol) were dissolved in abs. N,N-dimethylformamide (15 ml), sodium hydride (1.68 g, 42 mmol, 60% strength dispersion) was then added carefully a little at a time at a temperature of 10-15 C. and the mixture was stirred for another one and a half hours. Methanol and aqueous ammonium chloride solution were then added to the reaction mixture, and the aqueous phase was extracted intensively with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 1?-methylspiro[cyclopropane-1,3?-indol]-2?(1?H)-one (2500 mg, 92% of theory). 1H-NMR (400 MHz, CDCl3 delta, ppm) 7.25 (m, 1H), 7.03 (m, 1H), 6.91 (d, 1H), 6.83 (d, 1H), 3.30 (s, 3H), 1.73 (m, 2H), 1.52 (m, 2H). 1?-Methylspiro[cyclopropane-1,3?-indol]-2?(1?H)-one (2.50 g, 13 mmol) was added to glacial acetic acid (23 ml), and fuming nitric acid (4 ml) was then added slowly and carefully. The resulting reaction mixture was stirred at room temperature for 30 minutes and then slowly diluted with ice-water. The aqueous phase was then repeatedly extracted with ethyl acetate, and the combined organic phases were washed with saturated sodium carbonate solution and then dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 1?-methyl-5?-nitrospiro[cyclopropane-1,3?-indol]-2?(1?H)-one (1800 mg, 57% of theory) as a colorless solid. 1H-NMR (400 MHz, CDCl3 delta, ppm) 8.25 (dd, 1H), 7.74 (d, 1H), 6.97 (d, 1H), 3.36 (s, 3H), 1.88 (m, 2H), 1.69 (m, 2H). In the next step, 1?-methyl-5-nitrospiro[cyclopropane-1,3?-indol]-2?(1?H)-one (1.80 g, 8 mmol) and tin(II) chloride dihydrate (7.45 g, 33 mmol) were added together to abs. ethanol and stirred under argon at a temperature of 80 C. for 5 h. After cooling to room temperature, the reaction mixture was poured into ice-water and then adjusted to pH 12 using aqueous NaOH. The aqueous phase was then repeatedly extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 5?-amino-1?-methylspiro[cyclopropane-1,3?-indol]-2?(1?H)-one (1226 mg, 79% of theory) as a colorless solid. 1H-NMR (400 MHz, CDC138, ppm) 6.71 (d, 1H), 6.60 (dd, 1H), 6.25 (d, 1H), 3.52 (br. s, 2H, NH), 3.24 (t, 2H), 1.71 (m, 2H), 1.43 (m, 2H). In a round-bottom flask under argon, 5?-amino-1?-methylspiro[cyclopropane-1,3?-indol]-2?(1?H)-one (130 mg, 1.0 equiv.) and (3-bromophenyl)methanesulfonyl chloride (261 mg, 1.4 equiv.) were dissolved together in abs. acetonitrile, pyridine (0.11 ml, 2.0 equiv.) and dimethyl sulfoxide (0.03 ml, 0.60 mmol) were then added and the mixture was stirred at room temperature for 6 h. The reaction mixture was then concentrated under reduced pressure, water and dichloromethane were added to the residue that remained and the aqueous phase was extracted repeatedly with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 1-(3-bromophenyl)-N-(1?-methyl-2?-oxo-1?,2?-dihydrospiro[cyclopropane-1,3?-indol]-5-yl)methanesulfonamide (235 mg, 81% of theory) as a colorless solid. 1H-NMR (400 MHz, CDCl3 delta, ppm) 7.52 (m, 1H), 7.39 (m, 1H), 7.29 (m, 1H), 7.24 (m, 1H), 7.04 (m, 1H), 6.87 (d, 1H), 6.65 (d, 1H), 6.26 (s, 1H, NH), 4.13 (s, 2H), 3.30 (s, 3H), 1.78 (m, 2H), 1.54 (m, 2H). 13C-NMR (150 MHz, CDCl3 delta, ppm) 176.8, 141.7, 133.7, 132.6, 132.1, 130.8, 130.4, 129.5, 122.6, 120.8, 113.3, 108.3, 56.8, 27.4, 26.7, 19.7.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; FRACKENPOHL, Jens; BOJACK, GUIDO; HELMKE, HENDRIK; LEHR, STEFAN; MUELLER, THOMAS; WILLMS, LOTHAR; DITTGEN, JAN; SCHMUTZLER, DIRK; BICKERS, UDO; STREK, HARRY; BALTZ, RACHEL; (88 pag.)US2016/237035; (2016); A1;,
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Synthetic Route of 50727-04-3, A common heterocyclic compound, 50727-04-3, name is 5-Methoxyisoindoline-1,3-dione, molecular formula is C9H7NO3, 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.

2-bromo-5-trifluoromethylpyridine (224 mg, 1 mmol), triethylene diamine (224 mg, 2 mmol),4-methoxyphthalimide (354 mg, 2 mmol), potassium phosphate (434 mg, 2 mmol),N, N-dimethylacetamide (2 ml) was added to the dry reaction tube and suspended in an oil bath at 120 C for 24 h.After cooling the reaction system, 15 ml of water was added and the aqueous phase was extracted three times with 30 ml of ethyl acetate,The organic phases were combined and the solvent was evaporated under reduced pressure to give 338 mg of a colorless solid, 5-methoxy-2- (2-(4- (5-trifluoromethylpyridyl) 2-piperazinyl) 1-ethyl) isoindole-1,3-dione in a yield of 78%.

The synthetic route of 50727-04-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yichun University; Zhu Qiming; Chen Mingwei; (20 pag.)CN106317021; (2017); A;,
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Synthetic Route of 110568-64-4, These common heterocyclic compound, 110568-64-4, name is 6-Nitroisoindolin-1-one, 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.

Step 3: 5-aminoisoindolin-1-oneIron powder (2.51 g, 45 mmol), water (0.97 ml) and HCl (37percent, 0.74 ml), were added to a stirred suspension of the 5-nitroisoindolin-1-one (800 mg, 4.5 mmol) from step 2 of this example in EtOH (11.2 ml). The mixture was heated at 95 ¡ãC for 2h. Ammonia (7N in MeOH) was added (ImL) to make the pH of the mixture alkaline. The mixture was filtered to removed undissolved solids and the filter cake washed with EtOH (2×40 ml). The filtrate and organic washes were combined and concentrated in vacuum to give the titled compound.

Statistics shows that 6-Nitroisoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 110568-64-4.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WOOD, Harold, B.; ADAMS, Alan, D.; SZEWCZYK, Jason, W.; ZHANG, Yong; YANG, Meng; WO2011/19538; (2011); 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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, A new synthetic method of this compound is introduced below., Formula: C9H7NO3

General procedure: Intermediates (7) (140 mg, 1.2 equiv.), PyBOP (1.2 equiv.) and DIPEA (1.5 equiv.) were added toDMF and stirred at room temperature for 20 min. Then, intermediates (4a-d) (1.0 equiv.) was addedand stirred at room temperature for 4 h. After completion of the reaction, the reaction mixture wasquenched with saturated NaCl solution (25 mL). The aqueous phase was extracted with DCM (25 ¡Á3 mL). The DCM layer was combined and washed with brine solution (25 ¡Á 3 mL). The organic layerwas dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. Afterconcentration, the crude product was purified by silica gel column chromatograph using a methanolin DCM gradient (DCM: methanol= 60:1-5:1) yielded compounds 8i-l.

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Yan; Yang, Hongyu; Huang, Zhongwei; Tian, Sen; Li, Qihang; Du, Chenxi; Chen, Tingkai; Liu, Yang; Sun, Haopeng; Liu, Zongliang; Molecules; vol. 25; 3; (2020);,
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Related Products of 20870-79-5, The chemical industry reduces the impact on the environment during synthesis 20870-79-5, name is 5-Nitroindolin-2-one, I believe this compound will play a more active role in future production and life.

5-Amino-2-oxindole 5-Nitro-2-oxindole (6.3 g) was hydrogenated in methanol over 10% palladium on carbon to give 3.0 g (60% yield) of the title compound as a white solid.

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-Nitroindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US6350754; (2002); B2;,
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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. 2307-00-8, name is 5-Amino-2-methylisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Formula: C9H8N2O2

A mixture of 4-Bromo-N-cyclopropylmethyl-2-trifluoromethyl-benzenesulfonamide (150 mg), Pd(OAc)2 (9.5 mg), BINAP (26 mg)5cesium carbonate (164 mg) and 5- Amino-2-methyl-isoindole-l,3-dione (148 mg) in 15 ml toluene was reflaxed for 12 hours. The reaction mixture was eluted through a silica bed with Toluene and then with PE: EtOAc (1:1). The toluene fraction was discarded and the solvent of the PE: EtOAc fraction was removed under reduced pressure. The crude product was purified by Combiflash (linear gradient PE – THF). Yield 83 mg, 43 %.1H NMR (300 MHz, CDC13, rt) delta 0.13 (m, 2H5 CH2), 0.49 (m, 2H, CH2), 0.89 (m, IH, CH), 2.87 (t, broad, 2H, J= 7.2 Hz5 CH2), 3.18 (s, 3H5 CH3), 4.72 (t, broad, IH, NH), 6.75 (s, broad, IH, NH)5 6.98 (s, IH5 ArH)5 7.37 (dt, J= 8.1, J= 2.7, IH5 ArH)5 7.489 (d, IH5 J= 2.1, ArH)5 7.579 (d, IH5 J= 1.8, ArH)5 7.81 (d, IH5 J= 8.I5 ArH), and 8.14 (d, 2H, J= 8.7Hz5 ArH).MS: m/z 454.1 (M+)

The synthetic route of 2307-00-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMOS CORPORATION; WO2008/75353; (2008); A1;,
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Related Products of 114041-16-6, A common heterocyclic compound, 114041-16-6, name is 5,6-Dimethoxyisoindoline, molecular formula is C10H13NO2, 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.

A solution of 5,6-dimethoxyisoindoline 10e (0.12 g, 0.69 mmol) in acetic acid (1.4 mL) is vigorously stirred while cooling with a cold-water bath. Sulfuryl chloride (0.073 mL, 0.90 mmol) is added drop-wise. The resulting mixture is then warmed to room temperature and stirred for 3 h. The reaction mixture is diluted with diethyl ether (1.4 mL) and stirred for 30 minutes. The mixture is filtered and the solid isolated to give a mixture of the HCl salt of product 10h (0.134 g, 76%) and starting material (3:1 ratio respectively).

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; Gladius Pharmaceuticals, Inc.; SUTTON, Larry D.; ZAMBONI, Robert; BUREAU, Patrick; HASSANPOUR, Avid; MAMANI LAPARRA, Laura; VIDAL, Marc; WOO, Simon; ZHOU, Nancy; KEENAN, Richard M.; (127 pag.)US2019/100534; (2019); A1;,
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Synthetic Route of 1127-59-9, 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. 1127-59-9, name is 7-Methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The chemical synthesis route of the target IBT compounds is illustrated in Scheme 1. The IBTs 3 were synthesized by the reaction of isatin 1 and N-phenylhydrazinecarbothioamide 2 in an aqueous solution of ethanol and acetic acid under reflux [22,23]. Generally, equivalent 1 and 2 was dissolved in a solution of acetic acid/water/alcohol solution, and then the mixture was refluxed for approximate 5-6 h. The reaction mixture was subsequently cooled to room temperature and in most cases a yellow or orange solid precipitated out. This precipitate was filtered, washed with water, and then dried to give a crude product. Recrystallization from ethanol gave pure solid in high yields. 4.2.18 (Z)-N-(4-Chlorophenyl)-2-(7-methyl-2-oxoindolin-3-ylidene)hydrazinecarbothioamide (3-18) Yield 77percent; m.p.: 251-253 ¡ãC; yellow solid; 1H NMR (DMSO-d6, 400 MHz), delta 12.91 (s, 1H, NNH), 11.35 (s, 1H, NH), 10.86 (s, 1H, SCNH), 7.69-7.63 (m, 3H, J = 6.4 Hz, Ar1-H4, Ar2-H3 and Ar2-H5), 7.51-7.43 (m, 2H, J = 7.6 Hz, Ar2-H2 and Ar2-H6), 7.22 (d, 1H J = 7.6 Hz, Ar1-H6), 7.05 (t, 1H J = 8.0 Hz, Ar1-H5), 2.26 (s, 3H, CH3); 13C NMR (DMSO-d6, 101 MHz), delta 176.3, 163.1, 141.2, 137.4, 132.9, 132.7, 130.0, 128.2, 127.2, 122.3, 120.5, 119.5, 118.1, 15.8; IR: (KBr, nu/cm-1), 3310 (NN-H), 3173 (CON-H), 3057 (Ar-H), 1696 (-CONH-), 1626 (C=N), 1595 and 1539 (Ar-C=C), 1209 (C=S), 1155 (N-N); Elemental analysis calculated for C16H13ClN4OS, C: 55.73, H: 3.80, N: 16.25, found C: 56.01, H: 4.10, N: 16.46; HRMS(MALDI) m/z: calculated. 345.0577, found 345.0565, [M + H]+.

The chemical industry reduces the impact on the environment during synthesis 7-Methylindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Xu-Meng; Guo, Hui; Li, Zai-Shun; Song, Fu-Hang; Wang, Wei-Min; Dai, Huan-Qin; Zhang, Li-Xin; Wang, Jian-Guo; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 419 – 430;,
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Related Products of 19155-24-9, A common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-2-one, molecular formula is C10H11NO, 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.

Example 1; 5-amino-1-ethyl-3,3-dimethylindolin-2-one; Compound a (38.4 g), prepared according to the procedures described in Robertson et. al. (J. Med. Chem. 29(10) 1832-1840 (1986)), was dissolved in 300 ml of conc. sulfuric acid using mechanical stirring and cooled using a -40¡ã C. bath until the reaction became very thick. A solution of 10.1 ml of fuming nitric acid and 50 ml of conc. sulfuric acid was added dropwiseover 30 min. The reaction was allowed to warm to ambient temperature with stirring for 12 hours. The reaction mixture was poured into ice water and compound b was collected by filtration and dried (yield: 31 g).

The synthetic route of 19155-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rawson, Thomas E.; Safina, Brian; Dotson, Jennafer; Zhou, Aihe; Aliagas-Martin, Ignacio; Halladay, Jason; Liang, Jun; Rueth, Matthias; Zhu, Bing-Yan; US2007/37791; (2007); 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. 84575-27-9, name is 7-Methoxyindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H7NO3

To 7-methoxy-1 H-indole-2,3-dione (SM-1 b) (500 mg; 2.82 mmol) in DMF (5.0 mL) is added K2C03 (585 mg; 4.23 mmol) in one portion. The reaction mixture is stirred at rt for 30 min before iodomethane (SM-5b) (0.230 mL; 3.67 mmol) is added and stirring is continued at rt for 2 h. The reaction mixture is poured into water, acidified with 4 N HCIaq. and stirred for 30 min. The resulting precipitate is collected by filtration, washed with water and dried in vacuo to give 7-methoxy-1 -methyl-2,3-dihydro-1 H-indole-2,3-dione (A-2a) (HPLC-MS: tRet. = 0.87 min; MS (M+H)+ = 192; method 1 ).

The synthetic route of 84575-27-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; STEURER, Steffen; DAHMANN, Georg; KERRES, Nina; KOEGL, Manfred; (210 pag.)WO2018/108704; (2018); A1;,
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