Sodium hydride → HCID 59625674、化合物

HRID 403318

反応式

HRID 403318 の反応式
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[F:16][CH:17]([F:20])[CH2:18]I>CN(C=O)C>[F:16][CH:17]([F:20])[CH2:18][N:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 2737635methyl 1H-indole-5-carboxylateHCID 38335651,1-Difluoro-2-iodoethane

生成物 1

HCID 59625674HCID 59625674、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

To a suspension of NaH (60% dispersion in mineral oil, 59 mg, 1.48 mmol) in DMF (2 mL) was slowly added a solution of 1H-indole-5-carboxylic acid methyl ester 19a (200 mg, 1.14 mmol) in DMF (1 mL) at 0° C. The resulting solution was stirred at 0° C. for 20 min and 1,1-difluoro-2-iodoethane 23a (263 mg, 1.37 mmol) was added. The reaction was warmed to room temperature and stirred for 2 h. The reaction was quenched with water and extracted with EtOAc. The organic layer was concentrated and purified by flash column chromatography (silica gel, 20% EtOAc/hexanes) to afford compound 23b.

後処理

  1. temperatureThe reaction was warmed to room temperature
  2. stirringstirred for 2 h
  3. customThe reaction was quenched with water
  4. extractionextracted with EtOAc
  5. concentrationThe organic layer was concentrated
  6. custompurified by flash column chromatography (silica gel, 20% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-8e201d7d630d40bb9bc71292aad00fd1
出典データセット
uspto-grants-2014_06
特許番号
US08748417B2

関連ノート

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