Dimethylformamide → 2-chloro-3-(1-cyanocyclopropyl)-N-{2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide

HRID 1800657Notes

Reaction equation

HRID 1800657 reaction equation
[Cl:1][C:2]1[C:18]([C:19]2([C:22]#[N:23])[CH2:21][CH2:20]2)=[CH:17][CH:16]=[CH:15][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:8]=1[F:14])=[O:5].Cl[C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:1][C:2]1[C:18]([C:19]2([C:22]#[N:23])[CH2:21][CH2:20]2)=[CH:17][CH:16]=[CH:15][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][N:26]=2)[CH:10]=[CH:9][C:8]=1[F:14])=[O:5]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 57387082HCID 57387082, compound

Product 1

HCID 573842802-chloro-3-(1-cyanocyclopropyl)-N-{2-fluoro-5-[(5-nitropyridin-2-yl)oxy]phenyl}benzamideYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-chloro-3-(1-cyanocyclopropyl)-N-(2-fluoro-5-hydroxyphenyl)benzamide (23.0 g, 69.6 mmol), 2-chloro-5-nitropyridine (12.2 g, 77.1 mmol), potassium carbonate (11.5 g, 83.1 mmol) and N,N-dimethylformamide (70 mL) was stirred at room temperature for 4 hr. To the reaction mixture were added N,N-dimethylformamide (130 mL) and water (250 mL), and the mixture was stirred at room temperature for 1 hr. The precipitate was collected by filtration, washed with water (200 mL), and dried under reduced pressure to give the title compound (29.3 g, 93%) as a gray powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water (200 mL)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-64675ede6c5c4881a7583b38ad1acc43
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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