Potassium Carbonate → Methyl 2-[3-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)phenoxy]-5-nitrobenzoate

HRID 1097518Notes

Reaction equation

HRID 1097518 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:19]=[CH:20][CH:21]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2].F[C:23]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([C:3]([C:6]1[CH:7]=[C:8]([C:9]([NH:11][C:12]2[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=2)[O:18][C:23]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][C:24]=2[C:25]([O:27][CH3:28])=[O:26])=[O:10])[CH:19]=[CH:20][CH:21]=1)([CH3:5])[CH3:4])#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11217860Methyl 2-Fluoro-5-nitrobenzoateHCID 57386825HCID 57386825, compound

Product 1

HCID 66810330Methyl 2-[3-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)phenoxy]-5-nitrobenzoateYield 103.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(1-cyano-1-methylethyl)-N-(3-hydroxyphenyl)benzamide (5.0 g, 17.8 mmol) produced in Example 1(i) and methyl 2-fluoro-5-nitrobenzoate (3.55 g, 17.8 mmol) in N,N-dimethylformamide (50 mL) was added potassium carbonate (3.68 g, 26.7 mmol), and the mixture was stirred at room temperature for 16 hr. Insoluble material was filtered off and washed with ethyl acetate (200 mL). The filtrate and washings were combined and washed successively with 5% aqueous sodium hydrogen carbonate solution (200 mL) and saturated brine (200 mL), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (eluate: ethyl acetate), and the obtained solution was concentrated under reduced pressure to give the title compound (8.45 g, 98%) as a white powder.

Workup

  1. filtrationInsoluble material was filtered off
  2. washwashed with ethyl acetate (200 mL)
  3. washwashed successively with 5% aqueous sodium hydrogen carbonate solution (200 mL) and saturated brine (200 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationInsoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by basic silica gel column chromatography (eluate: ethyl acetate)
  8. concentrationthe obtained solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8d5d709b011a475590d9bd380143f302
Source dataset
uspto-grants-2012_03
Patent number
US08143258B2

Reaction notes

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