Trityl chloride → 3H-Imidazo[4,5-b]pyridine, 6-bromo-3-(triphenylmethyl)-

HRID 241018

反応式

HRID 241018 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[NH:10][CH:9]=[N:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[C:13]1([C:19](Cl)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[CH:9][N:8]([C:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:5]2=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 9115786-Bromo-4H-imidazo[4,5-b]pyridine

生成物 1

HCID 668203913H-Imidazo[4,5-b]pyridine, 6-bromo-3-(triphenylmethyl)-収率 37.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of 6-bromo-1H-imidazo[4,5-b]pyridine (2.7 g, 11.0 mmol) in dimethylformamide (30 mL) at 0° C. was added 60% sodium hydride in mineral oil (0.53 g, 13.2 mmol) and the reaction mixture was stirred for 30 minutes, followed by the addition of a solution of triphenylmethyl chloride (3.2 g, 11.55 mmol) in dimethylformamide (5 mL). The reaction mixture was stirred at room temperature for 24 hours then quenched by the careful addition of water then partitioned with ethyl acetate (250 mL). The organic phase was washed with 10% aqueous citric acid (2×, 100 mL), brine (100 mL), saturated sodium bicarbonate (100 mL), brine (100 mL) then dried over anhydrous sodium sulfate, filtered and concentrated. Silica gel chromatography (hexane ethyl acetate 9:1 to 4:1) provided 6-bromo-3-trityl-3H-imidazo[4,5-b]pyridine (1.8 g, 37%). 1H NMR (400 MHz, CDCl3): 8.18 (d, 1H), 8.14 (d, 1H), 8.02 (s, 1H), 7.36-7.28 (m, 10H), 7.18-7.14 (m, 5H) and 6-bromo-1-trityl-1H-imidazo[4,5-b]pyridine (2.9 g, 60%) 1H NMR (400 MHz, CDCl3): 8.50 (d, 1H), 8.14 (s, 1H), 7.38-7.34 (m, 10H), 7.16-7.12 (m, 5H), 6.84 (d, 1H).

後処理

  1. stirringThe reaction mixture was stirred at room temperature for 24 hours
  2. customthen quenched by the careful addition of water
  3. customthen partitioned with ethyl acetate (250 mL)
  4. washThe organic phase was washed with 10% aqueous citric acid (2×, 100 mL), brine (100 mL), saturated sodium bicarbonate (100 mL), brine (100 mL)
  5. dry with materialthen dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-09588231a0d243188ff5c4647a272729
出典データセット
uspto-grants-2014_02
特許番号
US08648066B2

関連ノート

読み込み中…