Water → 3-(4-bromo-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carbonitrile

HRID 1699819ノート

反応式

HRID 1699819 の反応式
[CH3:1][C:2]1[N:12]=[C:5]2[NH:6][C:7]([C:10]#[N:11])=[CH:8][CH:9]=[C:4]2[N:3]=1.[H-].[Na+].CS(O[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=1[Cl:28])(=O)=O.O>CN(C)C=O>[Br:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:12]2[C:5]3=[N:6][C:7]([C:10]#[N:11])=[CH:8][CH:9]=[C:4]3[N:3]=[C:2]2[CH3:1])=[C:22]([Cl:28])[CH:23]=1.[Br:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:3]2[C:4]3[C:5](=[N:6][C:7]([C:10]#[N:11])=[CH:8][CH:9]=3)[N:12]=[C:2]2[CH3:1])=[C:22]([Cl:28])[CH:23]=1

参加物

7

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 220586494-Bromo-2-chlorobenzyl methanesulfonateHCID 178432171HCID 178432171、化合物

生成物 2

HCID 223877943-(4-bromo-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carbonitrileHCID 223883031-(4-bromo-2-chlorobenzyl)-2-methyl-1H-imidazo[4,5-b]pyridine-5-carbonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of 2-methylimidazo[4,5-b]pyridine-5-carbonitrile (200 mg) in N,N-dimethylformamide (2 ml) was added sodium hydride (70% in mineral oil, 55 mg) under ice-cooling, and the mixture was stirred for 30 min. To this reaction mixture was added 4-bromo-2-chlorobenzyl methanesulfonate (450 mg), and the mixture was stirred for 2 hr at room temperature. The reaction mixture was poured into water and the product was extracted three times with ethyl acetate. The organic layers were combined and washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was subjected to silica gel column chromatography (dichloromethane/ethyl acetate=5/1) to give two isomers, 3-(4-bromo-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carbonitrile (Rf 0.4, 233 mg) and 1-(4-bromo-2-chlorobenzyl)-2-methyl-1H-imidazo[4,5-b]pyridine-5-carbonitrile (Rf 0.1, 163 mg) as a white powder and a pale-yellow powder.

後処理

  1. temperaturecooling
  2. stirringthe mixture was stirred for 2 hr at room temperature
  3. extractionthe product was extracted three times with ethyl acetate
  4. washwashed successively with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-a8b88f6cabdd436ba873e13e4f916f9c
出典データセット
uspto-grants-2002_02
特許番号
US06348474B1

反応ノート

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