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

HRID 1874602ノート

反応式

HRID 1874602 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-596819845d3740ae8fca664dfa3f225a
出典データセット
uspto-grants-2012_11
特許番号
US08304557B2

反応ノート

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