Tributylphosphine → Ethyl 5-fluoro-1-[2-(pyridin-3-yl)ethyl]-1H-indole-2-carboxylate

HRID 19741ノート

反応式

HRID 19741 の反応式
N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[F:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:23]2.[N:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH2:40][CH2:41]O)[CH:35]=1.C(P(CCCC)CCCC)CCC>O1CCCC1>[F:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25]([CH2:41][CH2:40][C:36]1[CH:35]=[N:34][CH:39]=[CH:38][CH:37]=1)[C:24]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:23]2

参加物

6

反応物 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 805153-PyridineethanolHCID 2727899ethyl 5-fluoro-1H-indole-2-carboxylate

生成物 1

HCID 15978980Ethyl 5-fluoro-1-[2-(pyridin-3-yl)ethyl]-1H-indole-2-carboxylate収率 41.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 0.365 g (1.44 mmol) of 1,1′-(azodicarbonyl)dipiperidine in 10 ml of tetrahydrofuran is added dropwise to a solution of 0.2 g (0.97 mmol) of ethyl 5-fluoro-1H-indole-2-carboxylate, 0.178 g (1.45 mmol) of 2-(pyrid-3-yl)ethanol and 0.36 ml (1.44 mmol) of tributylphosphine in 30 ml of tetrahydrofuran. The reaction mixture is stirred overnight at room temperature and then concentrated under reduced pressure and taken up in 50 ml of cyclohexane. The suspension is then filtered and the filtrate is chromatographed on a column of silica (eluent: dichloromethane/methanol). 0.125 g of the expected product is obtained.

後処理

  1. concentrationconcentrated under reduced pressure
  2. filtrationThe suspension is then filtered
  3. customthe filtrate is chromatographed on a column of silica (eluent: dichloromethane/methanol)

出典と根拠

ORDレコード
ord-c19877c546734a5aac91b4d7ba7a8526
出典データセット
uspto-grants-2010_06
特許番号
US07745467B2

反応ノート

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