N-(2,6-Difluoro-3-hydroxy-phenyl)-5-(3-fluorophenyl)-2-methyl-benzamide → 2,4-Difluoro-3-[[5-(3-fluorophenyl)-2-methyl-phenyl]methyl amino]phenol

HRID 1771597ノート

反応式

HRID 1771597 の反応式
[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[NH:10][C:11](=O)[C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)[CH:15]=[CH:14][C:13]=1[CH3:25]>C1COCC1>[F:1][C:2]1[C:3]([NH:10][CH2:11][C:12]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)[CH:15]=[CH:14][C:13]=2[CH3:25])=[C:4]([F:9])[CH:5]=[CH:6][C:7]=1[OH:8]

参加物

3

反応物 1

HCID 89443775N-(2,6-Difluoro-3-hydroxy-phenyl)-5-(3-fluorophenyl)-2-methyl-benzamide

生成物 1

HCID 894454532,4-Difluoro-3-[[5-(3-fluorophenyl)-2-methyl-phenyl]methyl amino]phenol収率 86%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
55 °C

実験手順

To a solution of N-(2,6-difluoro-3-hydroxy-phenyl)-5-(3-fluorophenyl)-2-methyl-benzamide (150 mg, 0.42 mmol, 1.0 eq) in THF (5 mL) was added dropwise a solution of BH3 (1 M in THF, 3 mL, 3 mmol, 7 eq). The reaction was heated at 55° C. under N2 for 2 h, and then quenched by the addition of 1M HCl. The aqueous layer was extracted with EtOAc and the combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo to give compound the title compound as a solid (124 mg, 86%).

後処理

  1. customquenched by the addition of 1M HCl
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washthe combined organic extracts were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

出典と根拠

ORDレコード
ord-609720c0244f485caa5715ccb40148f8
出典データセット
uspto-grants-2016_02
特許番号
US09249085B2

反応ノート

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