Triethylamine → ethyl 1H-indol-5-ylcarbamate

HRID 1467995ノート

反応式

HRID 1467995 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH2:10])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(N(CC)CC)C.[CH2:18]([O:20][C:21](Cl)=[O:22])[CH3:19]>ClCCl>[CH2:18]([O:20][C:21](=[O:22])[NH:10][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][CH:2]=[CH:3]2)[CH3:19]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 788675-Aminoindole

生成物 1

HCID 54033885ethyl 1H-indol-5-ylcarbamate収率 35.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 1H-indol-5-amine (11 g, 83.2 mmol) and triethyl amine (25.22 g, 250 mmol) in dichloromethane (110 mL) at −10° C., ethyl-chloro-formate (13.5 g 124.8 mmol) was added dropwise and stirred at 0° C. for 2-3 h. The reaction was quenched with water and the mixture was extracted with ethyl acetate. The organic layer was concentrated in vacuo and the resultant residue was purified by flash column chromatography to give ethyl-1H-indol-5-ylcarbamate (5.980 g, 35.2%); MS: 205 (M+1).

後処理

  1. customThe reaction was quenched with water
  2. extractionthe mixture was extracted with ethyl acetate
  3. concentrationThe organic layer was concentrated in vacuo
  4. customthe resultant residue was purified by flash column chromatography

出典と根拠

ORDレコード
ord-7af1d86742654a98bab712e45762843f
出典データセット
uspto-grants-2015_04
特許番号
US09000175B2

反応ノート

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