P-Anisidine → 3-Cyano-2-fluoro-4-methoxy-N-(4-methoxyphenyl)benzamide

HRID 2054904Notes

Reaction equation

HRID 2054904 reaction equation
[C:1]([C:3]1[C:4]([F:14])=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O)#[N:2].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=1.C(N(CC)C(C)C)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[C:1]([C:3]1[C:4]([F:14])=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([NH:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=1)=[O:8])#[N:2]

Participants

7

Reactant 4

HCID 7732P-AnisidineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 596566313-cyano-2-fluoro-4-methoxybenzoic acid

Product 1

HCID 596567063-Cyano-2-fluoro-4-methoxy-N-(4-methoxyphenyl)benzamideYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of the above benzoic acid derivative (360 mg, 1.85 mmol), p-anisidine (315 mg, 2.56 mmol), N,N-diisopropylethylamine (1.34 mL, 7.68 mmol) and PyBop (1.6 g, 3.1 mmol) in dry DMF (7 mL) was stirred at room temperature overnight and then diluted with water (40 mL). The precipitates were filtered, washed with water three times, and dried in vacuo to give 3-cyano-2-fluoro-4-methoxy-N-(4-methoxy-phenyl)-benzamide (540 mg, 98%).

Workup

  1. filtrationThe precipitates were filtered
  2. washwashed with water three times
  3. customdried in vacuo

Sources & evidence

ORD record
ord-8e195ff7893f42c1ad7ea6ae6c64e325
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Reaction notes

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