Water → HCID 68417567, compound

HRID 1800581Notes

Reaction equation

HRID 1800581 reaction equation
[Cl:1][C:2]1[C:19]([C:20]2([C:23]#[N:24])[CH2:22][CH2:21]2)=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([OH:13])[C:10]([F:14])=[CH:9][C:8]=1[F:15])=[O:5].Cl[C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][N:27]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:1][C:2]1[C:19]([C:20]2([C:23]#[N:24])[CH2:22][CH2:21]2)=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][N:27]=2)[C:10]([F:14])=[CH:9][C:8]=1[F:15])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 684178522-chloro-3-(1-cyanocyclopropyl)-N-(2,4-difluoro-5-hydroxyphenyl)benzamide

Product 1

HCID 68417567HCID 68417567, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-chloro-3-(1-cyanocyclopropyl)-N-(2,4-difluoro-5-hydroxyphenyl)benzamide (4.20 g, 12 mmol), 2-chloro-5-nitropyridine (1.9 g, 12 mmol) and potassium carbonate (1.66 g, 12 mmol) in N,N-dimethylformamide (20 mL) was stirred at room temperature overnight. The reaction mixture was poured into water (200 mL), and the mixture was extracted with ethyl acetate (100 mL×2). The ethyl acetate layers were combined, and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100→50/50), and crystallized from diethyl ether to give the title compound (5.20 g, 92%) as a yellow powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (100 mL×2)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100→50/50)
  6. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-5dddd4b9a1794eaa9a6a656e83840da5
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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