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[ CAS No. 1528-41-2 ]

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Chemical Structure| 1528-41-2
Chemical Structure| 1528-41-2
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CAS No. :1528-41-2 MDL No. :MFCD09953133
Formula : C11H11NO2 Boiling Point : 304.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :189.21 g/mol Pubchem ID :279718
Synonyms :

Safety of [ 1528-41-2 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P280-P305+P351+P338-P311 UN#:3439
Hazard Statements:H302+H312-H315-H319-H331-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1528-41-2 ]

  • Upstream synthesis route of [ 1528-41-2 ]
  • Downstream synthetic route of [ 1528-41-2 ]

[ 1528-41-2 ] Synthesis Path-Upstream   1~20

  • 1
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YieldReaction ConditionsOperation in experiment
47% With dmap; bis(η3-allyl-μ-chloropalladium(II)); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,3,5-trimethyl-benzene at 140℃; for 20 h; Inert atmosphere General procedure: after standard cycles of evacuation and back-filling with dry and pure nitrogen, an oven-dried Schlenk tube equipped with a magnetic stirring bar was charged with Pd source (see Table 1, Table 2, Table 3 and Table 4), ligand (see Table 1, Table 2, Table 3 and Table 4), N,N-dimethylpyridin-4-amine (DMAP, see Table 1, Table 2, Table 3 and Table 4), and ethyl potassium malonate (see Table 1, Table 2, Table 3 and Table 4). The tube was evacuated and backfilled with argon (this procedure was repeated three times). Under a counter flow of argon, aryl halide (see Table 1, Table 2, Table 3 and Table 4) and solvent (see Table 1, Table 2, Table 3 and Table 4) were added by syringe. The tube was sealed and stirred at room temperature for 10 min. Then the tube was connected to the Schlenk line, which was full of argon, stirred in a preheated oil bath (140-150 °C) for the appointed time (20-25 h). Upon completion of the reaction, the mixture was cooled to room temperature and diluted with diethyl ether, and the yields were determined by gas chromatography using 1,3-dimethoxybenzene as the internal standard.
Reference: [1] Tetrahedron, 2012, vol. 68, # 9, p. 2113 - 2120
[2] Angewandte Chemie - International Edition, 2011, vol. 50, # 19, p. 4470 - 4474
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YieldReaction ConditionsOperation in experiment
66.5% With copper(l) iodide In 1-methyl-pyrrolidin-2-one at 160 - 180℃; for 7 h; Inert atmosphere Preparation 56 ethyl 2-(4-cyanophenyl)acetate [0247] Combined ethyl 2-(4-bromophenyl)acetate (30 g, 0.123 mol) and MP (200 mL). Then CuCN (33 g, 0.370 mol) was added in portions and then degassed and refilled with nitrogen three times. Then Cul (4.7 g, 0.0247mol) was added in one portion. The reaction was degassed and refilled with nitrogen three times and then heated to 160°C for 4 hours. Then the reaction was heated to 180°C for another 3 hours. The solution was then cooled to room temperature and diluted with EtOAc (500 mL) and water (500 mL). After stirring for 10 mins, the reaction was filtered and the aqueous layer was extracted with EtOAc (500 mLx2). The combined organic layers were washed with brine, dried over Na2S04 and concentrated to dryness to give the title compound (31 g, 66.5percent) as a brown solid.
Reference: [1] Patent: WO2014/160810, 2014, A1, . Location in patent: Paragraph 0246; 0247
  • 3
  • [ 623-00-7 ]
  • [ 6148-64-7 ]
  • [ 1528-41-2 ]
YieldReaction ConditionsOperation in experiment
64% With dmap; bis(η3-allyl-μ-chloropalladium(II)); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,3,5-trimethyl-benzene at 140℃; for 20 h; Inert atmosphere General procedure: after standard cycles of evacuation and back-filling with dry and pure nitrogen, an oven-dried Schlenk tube equipped with a magnetic stirring bar was charged with Pd source (see Table 1, Table 2, Table 3 and Table 4), ligand (see Table 1, Table 2, Table 3 and Table 4), N,N-dimethylpyridin-4-amine (DMAP, see Table 1, Table 2, Table 3 and Table 4), and ethyl potassium malonate (see Table 1, Table 2, Table 3 and Table 4). The tube was evacuated and backfilled with argon (this procedure was repeated three times). Under a counter flow of argon, aryl halide (see Table 1, Table 2, Table 3 and Table 4) and solvent (see Table 1, Table 2, Table 3 and Table 4) were added by syringe. The tube was sealed and stirred at room temperature for 10 min. Then the tube was connected to the Schlenk line, which was full of argon, stirred in a preheated oil bath (140-150 °C) for the appointed time (20-25 h). Upon completion of the reaction, the mixture was cooled to room temperature and diluted with diethyl ether, and the yields were determined by gas chromatography using 1,3-dimethoxybenzene as the internal standard.
Reference: [1] Tetrahedron, 2012, vol. 68, # 9, p. 2113 - 2120
  • 4
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  • [ 143-33-9 ]
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Reference: [1] Journal of the American Chemical Society, 2003, vol. 125, # 10, p. 2890 - 2891
  • 5
  • [ 557-21-1 ]
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YieldReaction ConditionsOperation in experiment
49% With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamideReflux Step 0 (Intermediate A): see example 85.[0556]Step 1: To a stirred solution of 2-(4-bromophenyl)acetic acid (2 g, 9.3 mmol) in ethanol (10 mL) were added sulfuric acid (0.3 mL). The reaction mixture was refluxed for overnight and cooled to room temperature. The solvent was evaporated. The residue was dissolved with ethylacetate and neutralized with NaHCO3. The organic layer was washed with water two times, then dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. ethyl 2-(4-bromophenyl)acetate (2.1 g) was obtained as 91percent yield.[0557]Step 2: To a stirred solution of ethyl 2-(4-bromophenyl)acetate (2.1 g, 8.445 mmol) in anhydrous dimethylformamide were added zinc cyanide (1.5 g, 12.668 mmol) and tetrakis(triphenylphosphine) palladium (1.0 g, 0.845 mmol). The reaction mixture was refluxed for overnight then cooled to room temperature. The mixture was filtered using celite pad and the filtrate was evaporated. The residue was diluted with ethylacetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filterate was concentrated under reduced pressure to get the crude. The crude was purified by column chromatography. Ethyl 2-(4-cyanophenyl)acetate (0.8 g) was obtained as 49percent yield.[0558]Step 3: To a stirred solution of ethyl 2-(4-cyanophenyl)acetate (0.8 g, 4.101 mmol) in anhydrous dimethylformamide were added 60percent sodium hydride (180 mg, 4.511 mol) and Iodo methane were added after 10 min with an ice bath. The reaction mixture was stirred for 1 h hours, quenched with water and extracted with ethylacetate which is washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filterate was concentrated under reduced pressure. The residue was purified by column chromatography. Ethyl 2-(4-cyanophenyl)propanoate (453 mg) was obtained as 48percent[0559]Step 4: To a stirred solution of ethyl 2-(4-cyanophenyl)propanoate (453 mg, 1.968 mmol) in co-solvent with tetrahydrofuran and water (1:1) were added sodium hydroxide (197 mg, 4.919 mmol). The reaction mixture was stirred for overnight at room temperature, then acidified to pH 3-4 with acetic acid. The residue was diluted with ethylacetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude 2-(4-cyanophenyl)propanoic acid (422 mg) was obtained as 99percent yield.[0560]Step 5: To a stirred solution of 2-(4-cyanophenyl)propanoic acid (148 mg, 0.85 mmol) in acetonitrile were added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (243 mg, 1.27 mmol), 1-hydroxybenzotriazole (171 mg, 1.27 mmol), (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (247 mg, 0.93 mmol) and triethylamine (0.29 mL, 2.11 mmol). The reaction mixture was stirred for overnight at room temperature. The mixture was diluted with ethylacetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. 2-(4-Cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (311 mg) was obtained as 87percent yield.[0561]Step 6: To a stirred solution of 2-(4-cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (305 mg, 0.72 mmol) in ethanol was cooled to 0° C. and added NiCl2.6H2O (17 mg, 0.072 mmol) and stirred more then 15 min. Sodium borohydride (191 mg, 5.04 mmol) was then added in small portions. The reaction was exothermic and effervescent. The resulting reaction mixture was allowed to warm to room temperature and left to stir for 2 hour. The mixture was filtered using celite pad. The filtrate was concentrated was evaporated. The residue was dissolved in ethylacetate and washed with water and brine, but when it does not separate easily, small amount of 1N HCl and saturated NaHCO3 was used. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. 2-(4-(Aminomethyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (167 mg) was obtained as 64percent yield.[0562]Step 7: To a stirred solution of 2-(4-(aminomethyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (167 mg, 0.39 mmol) in dichloromethane the intermediate (A) (117 mg, 0.39 mmol) and triethylamine (0.20 mL, 0.56 mmol) was added was stirred for overnight. The reaction mixture was stirred for overnight at room temperature. The mixture was diluted with dichloromethane and washed with water, brine, dried over magnesium sulfate and filtered. The filtrate was evaporated and the residue was purified by column chromatography. Tert-butyl N-(4-(1-oxo-1-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methylamino)propan-2-yl)benzyl)sulfamoylcarbamate (118 mg) was obtained as 50percent yield.[0563]Step 8: To a stirred solution of tert-butyl N-(4-(1-oxo-1-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methylamino)propan-2-yl)benzyl)sulfamoylcarbamate (118 mg, 0.19 mmol) in dichloromethane (5 mL) cooled by ice bath and trifluoroacetic acid (4.0 mL) was added. The reaction mixture was stirred for overnight. The mixture was diluted with dichloromethane and then washed with NaHCO3, brine, dried over magnesium sulfate and filtered. The filtrate was evaporated and purified by column chromatography. 2-(4-((Sulfamoylamino)methyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (example 88) (79 mg) was obtained as 79percent yield.[0564]1H NMR (300 MHz, CDCl3) δ 7.76 (d, 1H, J=7.86 Hz), 7.58 (s, 1H, J=7.86 Hz), 7.27-7.32 (m, 3H), 7.10-7.24 (m, 5H), 5.59 (bs, 1H), 4.69 (bs, 1H), 4.58 (s, 2H), 4.44 (d, 2H, J=6.03 Hz), 4.26 (d, 2H, J=6.21 Hz), 3.50 (m, 1H), 2.38 (s, 3H), 1.46 (d, 3H, J=7.14 Hz).
38% With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamideReflux; Inert atmosphere Step 2: To a solution of ethyl 2-(4-bromophenyl)acetate (3.24 g, 13.32 mmol) in anhydrous dimethylformamide was added zinc cyanide (939 mg, 7.99 mmol), tetrakis(triphenylphosphine)palladium(0) (770 mg, 0.67 mmol).
The reaction mixture was refluxed for overnight under N2. TLC showed complete consumption of starting material.
The mixture was filtered through celite bed and the filterate was concentrated under reduced pressure.
The mixture was extracted with ethyl acetateand washed with water and brine.
The extract was dried over magnesium sulfate and concentrated under reduced pressure to afford crude which was purified by column chromatography to afford ethyl 2-(4-(iminomethyl)phenyl)acetate. (962 mg, 38percent)
Reference: [1] Patent: US2013/79377, 2013, A1, . Location in patent: Paragraph 0554; 0557
[2] Patent: US2013/79320, 2013, A1, . Location in patent: Paragraph 0473; 0475
  • 6
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  • [ 681-94-7 ]
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Reference: [1] Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 11, p. 3383 - 3384
  • 7
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  • [ 1528-41-2 ]
YieldReaction ConditionsOperation in experiment
49% With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamideReflux Step 2: To a stirred solution of ethyl 2-(4-bromophenyl)acetate (2.1 g, 8.445 mmol) in anhydrous dimethylformamide were added zinc cyanide (1 .5 g, 12.668 mmol) and tetrakis(triphenylphosphine) palladium (1 .0 g, 0.845 mmol). The reaction mixture was refluxed for overnight then cooled to room temperature. The mixture was filtered using celite pad and the filtrate was evaporated. The residue was diluted with ethylacteate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filterate was concentrated under reduced pressure to get the crude. The crude was purified by column chromatography. Ethyl 2-(4-cyanophenyl)acetate (0.8 g) was obtained as 49 percent yield.
Reference: [1] Patent: WO2013/45447, 2013, A1, . Location in patent: Page/Page column 83
  • 8
  • [ 64-17-5 ]
  • [ 5462-71-5 ]
  • [ 1528-41-2 ]
YieldReaction ConditionsOperation in experiment
89% for 3 h; Reflux Preparation 26
Ethyl (4-cyanophenyl)acetate
2-(4-cyanophenyl)acetic acid (1 g, 6.21 mmol) was dissolved in 1.25M solution of HCl in ethanol (11ml) and the mixture heated to reflux for 3h.
After cooling down to room temperature the solid formed was filtered off and dried in the vacuum oven. Yield=89percent.
LRMS: m/z 207 (M+17)+
Retention time: 5.33 min (Method B)
1H NMR (300 MHz, CHLOROFORM-d) d ppm 1.26 (t, 3 H) 3.64 (s, 2 H) 4.16 (q, 2 H) 4.90 (s, 2 H) 7.33 (d, J=8.51 Hz, 2 H) 7.60 (m, 2 H)
Reference: [1] Patent: EP2202232, 2010, A1, . Location in patent: Page/Page column 35; 36
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  • [ 5462-71-5 ]
  • [ 7664-93-9 ]
  • [ 1528-41-2 ]
Reference: [1] Patent: US5780642, 1998, A,
  • 10
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Reference: [1] European Journal of Organic Chemistry, 2013, # 20, p. 4255 - 4261
  • 11
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  • [ 126747-14-6 ]
  • [ 1528-41-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10510 - 10514[2] Angew. Chem., 2014, vol. 126, # 39, p. 10678 - 10682,5
  • 12
  • [ 623-00-7 ]
  • [ 141-97-9 ]
  • [ 1528-41-2 ]
  • [ 86369-43-9 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 18, p. 3289 - 3293
  • 13
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  • [ 141-97-9 ]
  • [ 1528-41-2 ]
Reference: [1] Tetrahedron, 1982, vol. 38, # 23, p. 3479 - 3483
  • 14
  • [ 623-03-0 ]
  • [ 105-53-3 ]
  • [ 1528-41-2 ]
Reference: [1] Advanced Synthesis and Catalysis, 2011, vol. 353, # 9, p. 1565 - 1574
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  • [ 105-53-3 ]
  • [ 1528-41-2 ]
Reference: [1] Advanced Synthesis and Catalysis, 2011, vol. 353, # 9, p. 1565 - 1574
  • 16
  • [ 1878-68-8 ]
  • [ 1528-41-2 ]
Reference: [1] Patent: WO2013/45447, 2013, A1,
  • 17
  • [ 557-21-1 ]
  • [ 1528-41-2 ]
Reference: [1] Patent: EP1229034, 2002, A1, . Location in patent: Page 123-124
  • 18
  • [ 1528-41-2 ]
  • [ 43153-12-4 ]
Reference: [1] Farmaco, Edizione Scientifica, 1988, vol. 43, # 7-8, p. 597 - 611
  • 19
  • [ 1528-41-2 ]
  • [ 62910-17-2 ]
  • [ 42383-05-1 ]
Reference: [1] Patent: US4207341, 1980, A,
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  • [ 362052-00-4 ]
Reference: [1] Patent: WO2013/45447, 2013, A1,
[2] Patent: US2013/79377, 2013, A1,
[3] Patent: US2013/79320, 2013, A1,
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