2-Fluoro-N-(6-fluoro-3-hydroxy-2-methyl-phenyl)-3-(3-fluorophenyl)-5-methyl-benzamide → 4-Fluoro-3-[[2-fluoro-3-(3-fluorophenyl)-5-methyl-phenyl]methylamino]-2-methyl-phenol

HRID 1771785ノート

反応式

HRID 1771785 の反応式
[F:1][C:2]1[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)=[CH:18][C:17]([CH3:27])=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[C:9]([OH:14])[C:8]=1[CH3:15])=O>C1COCC1>[F:13][C:12]1[CH:11]=[CH:10][C:9]([OH:14])=[C:8]([CH3:15])[C:7]=1[NH:6][CH2:4][C:3]1[CH:16]=[C:17]([CH3:27])[CH:18]=[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)[C:2]=1[F:1]

参加物

3

反応物 1

HCID 894453522-Fluoro-N-(6-fluoro-3-hydroxy-2-methyl-phenyl)-3-(3-fluorophenyl)-5-methyl-benzamide

生成物 1

HCID 894440664-Fluoro-3-[[2-fluoro-3-(3-fluorophenyl)-5-methyl-phenyl]methylamino]-2-methyl-phenol収率 93.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
60 °C

実験手順

To a stirred solution of 2-fluoro-N-(6-fluoro-3-hydroxy-2-methyl-phenyl)-3-(3-fluorophenyl)-5-methyl-benzamide (200 mg, 0.54 mmol, 1.0 eq) in THF (5 mL) under nitrogen was added a solution of BH3 (1M in THF, 3.0 mL, 3.0 mmol, 5.6 eq) dropwise over 5 min. the mixture was heated at 60° C. overnight, then the reaction cooled to room temperature and quenched by addition of aqueous NH4Cl. The reaction was further diluted with water and the aqueous layer was extracted with EtOAc. The combined organic extracts were dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 100:1 to 25:1) to give the title compound as a colorless oil (180 mg, 93%).

後処理

  1. temperaturethe reaction cooled to room temperature
  2. customquenched by addition of aqueous NH4Cl
  3. additionThe reaction was further diluted with water
  4. extractionthe aqueous layer was extracted with EtOAc
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue obtained
  9. customwas purified by column chromatography (petroleum ether:EtOAc, 100:1 to 25:1)

出典と根拠

ORDレコード
ord-174b132f14b3486f94830586f1da8d58
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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