Water → 2-(2-Methoxy-4-trifluoromethoxy-phenyl)-3-methyl-5-nitro-pyridine

HRID 2179996ノート

反応式

HRID 2179996 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][C:10]([F:13])([F:12])[F:11])[CH:6]=[CH:5][C:4]=1B(O)O.C([O-])([O-])=O.[K+].[K+].O.Cl[C:25]1[C:30]([CH3:31])=[CH:29][C:28]([N+:32]([O-:34])=[O:33])=[CH:27][N:26]=1>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][C:10]([F:13])([F:12])[F:11])[CH:6]=[CH:5][C:4]=1[C:25]1[C:30]([CH3:31])=[CH:29][C:28]([N+:32]([O-:34])=[O:33])=[CH:27][N:26]=1

参加物

7

反応物 4

HCID 962Water2 回HCID 11430Potassium CarbonateHCID 896482-Chloro-3-methyl-5-nitropyridineHCID 22490042(2-Methoxy-4-(trifluoromethoxy)phenyl)boronic acid

生成物 1

HCID 224900532-(2-Methoxy-4-trifluoromethoxy-phenyl)-3-methyl-5-nitro-pyridine

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
85 °C

実験手順

2-methoxy-4-trifluoromethoxybenzene boronic acid (72 g, 0.31 mol), K2CO3 (80.16 g, 0.58 mol) and water (100 ml) are added to a solution of 2-chloro-3-methyl -5-nitro-pyridine (50 g, 0.29 mol) in DME (500 ml) at room temperature. Pd(Ph3P)4 (3.35 g, 2.9 mmol) is added and the mixture is stirred at 85° C. for 19 hours. 500 ml of water is added and the mixture is extracted with EtOAc. The combined extracts are washed with brine and dried over Na2SO4. After removal of the solvent under reduced pressure, the residue is purified by flash column chromatography (hexane/EtOAc 9:1) to obtain 2-(2-methoxy-4-trifluoromethoxy-phenyl)-3-methyl-5-nitro-pyridine. Rf (hexane/EtOAc=9:1)=0.41.

後処理

  1. extractionthe mixture is extracted with EtOAc
  2. washThe combined extracts are washed with brine
  3. dry with materialdried over Na2SO4
  4. customAfter removal of the solvent under reduced pressure
  5. customthe residue is purified by flash column chromatography (hexane/EtOAc 9:1)

出典と根拠

ORDレコード
ord-314049de7972427d9e1f92cd737a6b08
出典データセット
uspto-grants-2005_05
特許番号
US06887875B2

反応ノート

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