Boron tribromide → N-(3,4-Difluorobenzyl)-6-hydroxy-2-isopropyl-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide

HRID 40155ノート

反応式

HRID 40155 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[F:33])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18]C)=[CH:15][CH:16]=2)[N:11]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[C:10]=1[CH:27]([CH3:29])[CH3:28])=[O:8].B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[F:33])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=2)[N:11]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[C:10]=1[CH:27]([CH3:29])[CH3:28])=[O:8]

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 59762372N-(3,4-Difluorobenzyl)-2-isopropyl-6-methoxy-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide2 回

生成物 1

HCID 59762365N-(3,4-Difluorobenzyl)-6-hydroxy-2-isopropyl-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide

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 solution of N-(3,4-difluorobenzyl)-2-isopropyl-6-methoxy-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide (Compound 200, 735 mg, 1.64 mmol) in CH2Cl2 (25 ml) at 0° C. was added BBr3 (1.0 M in CH2Cl2, 6.6 ml, 6.56 mmol) dropwise. The reaction was stirred for 1 h at 0° C. and 1 h at room temperature, quenched with ice, extracted with EtOAc, the organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→85% EtOAc-hexanes) to yield the title compound as a yellow oil.

後処理

  1. customquenched with ice
  2. extractionextracted with EtOAc
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel (0→85% EtOAc-hexanes)

出典と根拠

ORDレコード
ord-cb45213244f346f9910bab2d8cf738ef
出典データセット
uspto-grants-2013_09
特許番号
US08524917B2

反応ノート

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