4-Hydroxymethylpyridine → ethyl 5-fluoro-1-[(pyridin-4-yl)methyl]-1H-indole-2-carboxylate

HRID 1097254노트

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HRID 1097254 반응식
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][C:37]([CH2:40]O)=[CH:36][CH:35]=1>C1(C)C=CC=CC=1>[F:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25]([CH2:40][C:37]1[CH:38]=[CH:39][N:34]=[CH:35][CH:36]=1)[C:24]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:23]2

참가 물질

5

반응물 3

HCID 114724-HydroxymethylpyridineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 2727899ethyl 5-fluoro-1H-indole-2-carboxylate

생성물 1

HCID 15978981ethyl 5-fluoro-1-[(pyridin-4-yl)methyl]-1H-indole-2-carboxylate수율 74.1%

시약·촉매·용매 1

HCID 1140Toluene용매2회

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온도
20 °C

실험 절차

A solution of 5.5 g (21.72 mmol) of 1,1′-azodicarbonyl-dipiperidine, in solution in 15 ml of dry toluene, is added, under argon at 20° C., dropwise, to a solution of 3 g (14.48 mmol) of ethyl 5-fluoro-1H-indole-2-carboxylate, 2.37 g (21.72 mmol) of 4-pyridylcarbinol and 5.45 ml (21.72 mmol) of n-tributylphosphine in 200 ml of toluene. The mixture is stirred at 20° C. for 48 h. The reaction mixture is subsequently concentrated under reduced pressure. The residue is purified by silica column chromatography (eluent: heptane/ethyl acetate). 3.2 g of the expected product are thus isolated, which product is used as it is in the subsequent synthesis.

후처리

  1. concentrationThe reaction mixture is subsequently concentrated under reduced pressure
  2. customThe residue is purified by silica column chromatography (eluent: heptane/ethyl acetate)

출처 및 근거

ORD 기록
ord-c92795dc8c2d45d1a1b10dd8956f8ed7
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143248B2

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