Water → 4-Fluoro-3-[[5-(3-fluorophenyl)-2-methoxy-3-methyl-phenyl]methylamino]-2-methyl-phenol

HRID 1771758노트

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HRID 1771758 반응식
[F:1][C:2]1[C:7]([NH:8][C:9](=O)[C:10]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[CH:13]=[C:12]([CH3:23])[C:11]=2[O:24][CH3:25])=[C:6]([CH3:27])[C:5]([OH:28])=[CH:4][CH:3]=1.O>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:28])=[C:6]([CH3:27])[C:7]=1[NH:8][CH2:9][C:10]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[CH:13]=[C:12]([CH3:23])[C:11]=1[O:24][CH3:25]

참가 물질

4

반응물 2

HCID 962WaterHCID 89444099N-(6-Fluoro-3-hydroxy-2-methyl-phenyl)-5-(3-fluorophenyl)-2-methoxy-3-methyl-benzamide

생성물 1

HCID 894436934-Fluoro-3-[[5-(3-fluorophenyl)-2-methoxy-3-methyl-phenyl]methylamino]-2-methyl-phenol수율 22%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
60 °C

실험 절차

To a solution of N-(6-fluoro-3-hydroxy-2-methyl-phenyl)-5-(3-fluorophenyl)-2-methoxy-3-methyl-benzamide (450 mg, 1.17 mmol, 1.0 eq) in THF (6 mL) at 0° C. under N2 was added a solution of BH3 (1M in THF, 7.04 mL, 7.04 mmol, 6.0 eq). The reaction mixture was heated at 60° C. for 1 h. After cooling to 0° C., water was added dropwise and the aqueous layer extracted with EtOAc. The organic extract was washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by column chromatography (petroleum ether:EtOAc, 20:1 to 10:1) to give the title compound as a colorless oil (94 mg, 22%).

후처리

  1. temperatureAfter cooling to 0° C.
  2. extractionthe aqueous layer extracted with EtOAc
  3. extractionThe organic extract
  4. washwas 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, 20:1 to 10:1)

출처 및 근거

ORD 기록
ord-039380dbf52e4b8fb2cc9147c11d082b
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249085B2

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