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

HRID 1097254ノート

反応式

HRID 1097254 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][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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
20 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-c92795dc8c2d45d1a1b10dd8956f8ed7
出典データセット
uspto-grants-2012_03
特許番号
US08143248B2

反応ノート

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