HCID 89444094、化合物 → 2,4-Difluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-5-methyl-phenol

HRID 1771738ノート

反応式

HRID 1771738 の反応式
[F:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([CH3:9])=[C:4]([F:10])[C:3]=1[NH:11][C:12](=O)[C:13]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)[CH:16]=[CH:15][C:14]=1[F:26]>C1COCC1>[F:1][C:2]1[C:3]([NH:11][CH2:12][C:13]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)[CH:16]=[CH:15][C:14]=2[F:26])=[C:4]([F:10])[C:5]([CH3:9])=[CH:6][C:7]=1[OH:8]

参加物

3

反応物 1

HCID 89444094HCID 89444094、化合物

生成物 1

HCID 894451542,4-Difluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-5-methyl-phenol収率 75%

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

N-(2,6-difluoro-3-hydroxy-5-methyl-phenyl)-2-fluoro-5-(3-fluorophenyl)benzamide (285 mg, 0.76 mmol, 1.0 eq) was dissolved in THF (20 mL). A solution of BH3 (1M in THF, 4.56 mL, 4.56 mmol, 6.0 eq) was added and the reaction mixture heated at 60° C. under nitrogen for 2 h. After cooling, the reaction was quenched with water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by column chromatography (petroleum ether: EtOAc, 30:1 to 20:1) to give the title compound as a colorless oil (206 mg, 75%).

後処理

  1. temperatureAfter cooling
  2. customthe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography (petroleum ether: EtOAc, 30:1 to 20:1)

出典と根拠

ORDレコード
ord-b66b31eb8a6c481da7477f6da5579337
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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