Water → 3-(1-cyano-1-methylethyl)-N-{4-methyl-3-[(6-nitropyridin-3-yl)oxy]phenyl}benzamide

HRID 1874602Notes

Reaction equation

HRID 1874602 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:20]=[CH:21][CH:22]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([OH:19])[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2].Br[C:24]1[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[N:28][CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:20]=[CH:21][CH:22]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([O:19][C:24]2[CH:29]=[N:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[CH:13]=1)=[O:10])([CH3:4])[CH3:5])#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 8176205-Bromo-2-nitropyridineHCID 673134703-(1-cyano-1-methylethyl)-N-(3-hydroxy-4-methylphenyl)benzamide

Product 1

HCID 687235843-(1-cyano-1-methylethyl)-N-{4-methyl-3-[(6-nitropyridin-3-yl)oxy]phenyl}benzamideYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(1-cyano-1-methylethyl)-N-(3-hydroxy-4-methylphenyl)benzamide (8.35 g, 28.4 mmol), 5-bromo-2-nitropyridine (5.24 g, 25.8 mmol) and cesium carbonate (16.8 g, 51.6 mmol) in N,N-dimethylformamide (70 mL) was stirred at 60° C. for 4 hr. Water (200 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (100 mL, 2×50 mL). The combined organic layer was washed with saturated brine (30 mL) and dried over anhydrous magnesium 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 (NH silica gel, hexane/ethyl acetate=90/10→60/40), and fractions containing the desired product were concentrated under reduced pressure to give the title compound (6.70 g, 63%) as a yellow amorphous solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (100 mL, 2×50 mL)
  2. washThe combined organic layer was washed with saturated brine (30 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (NH silica gel, hexane/ethyl acetate=90/10→60/40), and fractions
  7. additioncontaining the desired product
  8. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-596819845d3740ae8fca664dfa3f225a
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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