Dimethylformamide → 3-(2-dimethylamino-ethyl)-1H-indole-5-carbaldehyde

HRID 507369

反応式

HRID 507369 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14].C([Li])(C)(C)C.CN([CH:24]=[O:25])C>CCOCC>[CH3:14][N:13]([CH3:15])[CH2:12][CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([CH:24]=[O:25])[CH:3]=2)[NH:7][CH:6]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 3602525-Bromo-N,N-DimethyltryptamineHCID 178418306HCID 178418306、化合物

生成物 1

HCID 99908943-(2-dimethylamino-ethyl)-1H-indole-5-carbaldehyde

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-75 °C

実験手順

To a solution of [2-(5-bromo-1H-indol-3-yl)-ethyl]-dimethyl-amine (Reference Example 2) (15 g, 56.1 mmol) in ether (450 mL), at −75° C. a solution of tert-butyl lithium (99 ml of 1.7 N solution in hexanes, 168 mmol) is added. The mixture is stirred for 50 minutes at −75° C., and then for 30 minutes at −30° C. To the obtained beige suspension, DMF (22.5 ml) is added during 15 minutes, and then the mixture is allowed to warm to ambient temperature. The mixture is poured on water and extracted with diethyl ether (500 mL). After washing the organic layer with brine (3 times 500 mL), and drying (sodium sulfate), removal of the solvent leaves the crude aldehyde, which is recrystallized, from toluene/hexane. Yield of the title compound: 9.9 g (81.8%) yellowish plates, mp=103° C.

後処理

  1. waitfor 30 minutes at −30° C
  2. temperatureto warm to ambient temperature
  3. additionThe mixture is poured on water
  4. extractionextracted with diethyl ether (500 mL)
  5. washAfter washing the organic layer with brine (3 times 500 mL)
  6. customdrying
  7. custom(sodium sulfate), removal of the solvent

出典と根拠

ORDレコード
ord-58ef21196a80456a8dd4ab4c15c6b676
出典データセット
uspto-grants-2010_08
特許番号
US07786156B2

関連ノート

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