Triethylamine → 6-Bromo-1-methyl-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile

HRID 75274ノート

反応式

HRID 75274 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[N:11]([CH3:12])[CH:10]=[CH:9][C:5]2=[N+:6]([O-])[CH:7]=1.C[CH2:14][N:15](CC)CC.C[Si](C#N)(C)C>ClCCCl>[Br:1][C:2]1[CH:3]=[C:4]2[N:11]([CH3:12])[CH:10]=[CH:9][C:5]2=[N:6][C:7]=1[C:14]#[N:15]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 867079626-Bromo-1-methyl-1H-pyrrolo[3,2-b]pyridine 4-oxide

生成物 1

HCID 867079636-Bromo-1-methyl-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile収率 76%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
80 °C

実験手順

To a stirred mixture of 6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridine 4-oxide (3.8 g 14 mmol), Et3N (19.51 mL, 140 mmol) and DCE (20 mL) was added trimethylsilyl cyanide (9.38 mL, 70.0 mmol). The reaction mixture was stirred at 80° C. for 5 h, subsequently concentrated in vacuo, and purified by silica gel chromatography eluting with EtOAc/DCM (1:1) to give the title compound as an off-white solid (2.50 g, 76%, 2 steps). ESI-MS m/z [M+H]+ calc'd for C9H6BrN3, 236, 238; found 236, 238.

後処理

  1. concentrationsubsequently concentrated in vacuo
  2. custompurified by silica gel chromatography
  3. washeluting with EtOAc/DCM (1:1)

出典と根拠

ORDレコード
ord-5bf51d1d43ca44e6be25d8924d2e8dd3
出典データセット
uspto-grants-2014_09
特許番号
US08835420B2

反応ノート

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