Dimethylformamide → 6-(trifluoromethyl)-1H-indole-4-carbaldehyde

HRID 913900ノート

反応式

HRID 913900 の反応式
Br[C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.C([Li])CCC.CN(C)[CH:22]=[O:23]>O1CCCC1.[Cl-].[Na+].O>[F:12][C:11]([F:14])([F:13])[C:9]1[CH:10]=[C:2]([CH:22]=[O:23])[C:3]2[CH:4]=[CH:5][NH:6][C:7]=2[CH:8]=1

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 247292314-Bromo-6-(trifluoromethyl)-1H-indoleHCID 178418339Butyllithium

生成物 1

HCID 575461946-(trifluoromethyl)-1H-indole-4-carbaldehyde

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
-78 °C

実験手順

A solution of 4-bromo-6-(trifluoromethyl)-1H-indole (5.23 g, 19.81 mmol) in tetrahydrofuran (20 ml) was cooled to −78 ° C. and treated slowly with n-butyllithium (1.6 M solution in hexanes, 39.6 ml, 63.4 mmol). The solution was stirred for 15 min at −78 ° C., and then treated with dimethylformamide (7.67 ml, 99 mmol), and stirred for 30 minutes more, allowing the reaction to warm to ambient temperature. The resulting solution was poured into brine and extracted with ethyl acetate. The pooled organics were dried over sodium sulfate and concentrated to give an amber oil. Column chromatography (ethyl acetate/hexanes gradient elution) afforded 1.17 g, (32%). 1H-NMR (CDCl3, 500 MHz) δ ppm 10.28 (s, 1H), 8.72 (br s, 1H), 7.93 (s, 1H), 7.88 (s, 1H), 7.58 (s, 1H), 7.42 (s, 1H). Mass spec.: 214.14 (MH)+.

後処理

  1. stirringstirred for 30 minutes more
  2. customthe reaction
  3. temperatureto warm to ambient temperature
  4. extractionextracted with ethyl acetate
  5. dry with materialThe pooled organics were dried over sodium sulfate
  6. concentrationconcentrated
  7. customto give an amber oil
  8. washColumn chromatography (ethyl acetate/hexanes gradient elution)
  9. customafforded 1.17 g, (32%)

出典と根拠

ORDレコード
ord-f6337f00924e41c691fd751eb480d7de
出典データセット
uspto-grants-2011_09
特許番号
US08026257B2

反応ノート

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