Benzyl Bromide → 1-Benzyl-4-bromo-6-fluoro-1H-indole-2-carboxylic acid methyl ester

HRID 18167

反応式

HRID 18167 の反応式
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[C:11]([Br:14])[CH:10]=[C:9]([F:15])[CH:8]=2)=[O:4].[H-].[Na+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:7]2[C:12]([CH:13]=1)=[C:11]([Br:14])[CH:10]=[C:9]([F:15])[CH:8]=2)=[O:4]

参加物

4

反応物 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 21867463Methyl 4-bromo-6-fluoro-1H-indole-2-carboxylate

生成物 1

HCID 593448921-Benzyl-4-bromo-6-fluoro-1H-indole-2-carboxylic acid methyl ester収率 34%

反応条件

温度
0 °C

実験手順

To a solution of 4-bromo-6-fluoro-1H-indole-2-carboxylic acid methyl ester (178 mg, 0.65 mmol) in 5 ml anhydrous dimethylformanide was added sodium hydride (52 mg of a 60% suspension in mineral oil, 1.3 mmol) portionwise at 0° C. The solution was stirred with a magnetic stirrer at 0° C. for 20 minutes. Benzyl bromide (0.17 ml, 1.43 mmol) was added in one portion and the reaction mixture was stirred at 0° C. for 30 minutes. The solution was allowed to warm to room temperature and the reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organic fractions were washed with water and brine. After drying over MgSO4, the organic fraction was concentrated in vacuo and resulting brown residue was purified by Preparative TLC (10% Ethyl acetate/Hexane) to give 80 mg 1-Benzyl-4-bromo-6-fluoro-1H-indole-2-carboxylic acid methyl ester as a yellow solid (34%). 1H NMR (CDCl3, 300 MHz) δ: 3.89 (s, 3H), 5.78 (s, 2H), 7.17 (m, 8H).

後処理

  1. stirringthe reaction mixture was stirred at 0° C. for 30 minutes
  2. temperatureto warm to room temperature
  3. customthe reaction mixture was partitioned between water and ethyl acetate
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washthe combined organic fractions were washed with water and brine
  6. dry with materialAfter drying over MgSO4
  7. concentrationthe organic fraction was concentrated in vacuo
  8. customresulting brown residue
  9. customwas purified by Preparative TLC (10% Ethyl acetate/Hexane)

出典と根拠

ORDレコード
ord-2e46238c6c614721b0f002b39e2ceb4a
出典データセット
uspto-grants-2010_06
特許番号
US07741326B2

関連ノート

読み込み中…