Sodium Cyanide → 6-bromo-2-(4-fluorophenyl)-2H-indazole-3-carbonitrile

HRID 1037560ノート

反応式

HRID 1037560 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[C:6]=2Cl.[C-:19]#[N:20].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[C:6]=2[C:19]#[N:20]

参加物

4

反応物 2

HCID 8929Sodium CyanideHCID 677760136-bromo-3-chloro-2-(4-fluorophenyl)-2H-indazole

生成物 1

HCID 675136096-bromo-2-(4-fluorophenyl)-2H-indazole-3-carbonitrile収率 54.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

To a stirred solution of compound (xiii) (4.49 g, 12.86 mmol) in DMF (50 mL) was added sodium cyanide (1.34 g, 27.73 mmol) at RT and the reaction mixture was then heated at 130° C. for 2 h. The reaction mixture was then diluted with saturated FeCl3 solution and extracted with EtOAc (3×75 mL). The combined organic layers were washed with water, dried (Na2SO4) and concentrated to give the crude product which was purified by column chromatography on 100-200 mesh silica gel eluting with EtOAc/hexane (2-4%) to give 6-bromo-2-(4-fluorophenyl)-2H-indazole-3-carbonitrile (xiv) (2.2 g, 50%) as white solid. ESI-MS m/z calculated for [M+H]+: 317.99; found: 317.90.

後処理

  1. extractionextracted with EtOAc (3×75 mL)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto give the crude product which
  6. customwas purified by column chromatography on 100-200 mesh silica gel eluting with EtOAc/hexane (2-4%)

出典と根拠

ORDレコード
ord-523d92fec85e47b1901a491436473d00
出典データセット
uspto-grants-2013_10
特許番号
US08546389B2

反応ノート

読み込み中…