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

HRID 1874593Notes

Reaction equation

HRID 1874593 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:17]([C:19]([C:22]1[CH:23]=[C:24]([CH:35]=[CH:36][CH:37]=1)[C:25]([NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([OH:34])[CH:29]=1)=[O:26])([CH3:21])[CH3:20])#[N:18].O>CN(C)C=O>[C:17]([C:19]([C:22]1[CH:23]=[C:24]([CH:35]=[CH:36][CH:37]=1)[C:25]([NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:2]2[CH:7]=[N:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH:29]=1)=[O:26])([CH3:21])[CH3:20])#[N:18]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonate2×HCID 8176205-Bromo-2-nitropyridineHCID 573868253-(1-cyano-1-methylethyl)-N-(3-hydroxyphenyl)benzamide

Product 1

HCID 687232483-(1-cyano-1-methylethyl)-N-{3-[(6-nitropyridin-3-yl)oxy]phenyl}benzamideYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5-bromo-2-nitropyridine (4.56 g, 22.4 mmol) and cesium carbonate (10.9 g, 33.6 mmol) in N,N-dimethylformamide (40 mL) was added dropwise a solution of 3-(1-cyano-1-methylethyl)-N-(3-hydroxyphenyl)benzamide (6.92 g, 24.6 mmol) in N,N-dimethylformamide (20 mL) over 30 min, and the mixture was stirred at room temperature for 28 hr. Cesium carbonate (3.63 g, 11.2 mmol) was added to the reaction mixture, and the mixture was further stirred with heating at 60° C. for 15 hr. Water (200 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate-hexane mixture (1:1, 200 mL, 3×50 mL). The combined organic layer was washed with saturated brine (30 mL) and dried over anhydrous magnesium sulfate. The insoluble material was removed by filtration, 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→50/50), and fractions containing the desired t product were concentrated under reduced pressure to give the title compound (6.01 g, 67%) as a yellow amorphous solid.

Workup

  1. stirringthe mixture was further stirred
  2. temperaturewith heating at 60° C. for 15 hr
  3. extractionthe mixture was extracted with ethyl acetate-hexane mixture (1:1, 200 mL, 3×50 mL)
  4. washThe combined organic layer was washed with saturated brine (30 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe insoluble material was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (NH silica gel, hexane/ethyl acetate=90/10→50/50), and fractions
  9. additioncontaining the desired t product
  10. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-e23ff09ceade403da951fbf3043edc39
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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