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

HRID 1771801ノート

反応式

HRID 1771801 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]([CH3:13])=[CH:11][CH:10]=[C:9]([OH:14])[C:8]=1[CH3:15])=O>C1COCC1>[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[CH2:4][NH:6][C:7]1[C:8]([CH3:15])=[C:9]([OH:14])[CH:10]=[CH:11][C:12]=1[CH3:13]

参加物

3

反応物 1

HCID 894438592-Fluoro-3-(3-fluorophenyl)-N-(3-hydroxy-2,6-dimethyl-phenyl)-5-methyl-benzamide

生成物 1

HCID 894438603-[[2-Fluoro-3-(3-fluorophenyl)-5-methyl-phenyl]methylamino]-2,4-dim ethyl-phenol収率 39%

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 solution of 2-fluoro-3-(3-fluorophenyl)-N-(3-hydroxy-2,6-dimethyl-phenyl)-5-methyl-benzamide (588 mg, 1.6 mmol, 1.0 eq) in THF (10 mL) at 0° C. under N2 was added a solution of BH3 (1M in THF, 9.6 mL, 9.6 mmol, 6.0 eq) dropwise. The reaction mixture was heated at 60° C. overnight. The reaction was cooled to room temperature, quenched with H2O and extracted with EtOAc. The combined organic layers were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 50:1 to 20:1) to give the title compound as white solid (220 mg, 39%)

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. customquenched with H2O
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue obtained
  9. customwas purified by column chromatography (petroleum ether:EtOAc, 50:1 to 20:1)

出典と根拠

ORDレコード
ord-14eab6e2d8054ced99bab4491e789af4
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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