1-{3,5-difluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indole → 1-(3,5-difluoro-4-hydroxyphenyl)-1H-indol-4-ol

HRID 2421260노트

반응식

HRID 2421260 반응식
[F:1][C:2]1[CH:3]=[C:4]([N:17]2[C:25]3[C:20](=[C:21]([O:26]CC4C=CC=CC=4)[CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18]2)[CH:5]=[C:6]([F:16])[C:7]=1[O:8]CC1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[F:16][C:6]1[CH:5]=[C:4]([N:17]2[C:25]3[CH:24]=[CH:23][CH:22]=[C:21]([OH:26])[C:20]=3[CH:19]=[CH:18]2)[CH:3]=[C:2]([F:1])[C:7]=1[OH:8]

참가 물질

4

반응물 1

HCID 596279281-{3,5-difluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indole

생성물 1

HCID 441932831-(3,5-difluoro-4-hydroxyphenyl)-1H-indol-4-ol수율 34.5%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

1-{3,5-difluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indole (D21) (299 mg, 0.678 mmoL) was dissolved in ethyl acetate (10 mL) and was hydrogenated at room temperature and atmospheric pressure in the presence of 10% palladium on charcoal (50% wet) (150 mg). After 21 hours the mixture was filtered and concentrated in vacuo. The crude product was purified by flash chromatography (Biotage SP4) eluting with a gradient of 0 to 100% Et2O in hexane to give the title compound (E11), (61 mg).

후처리

  1. customwas hydrogenated at room temperature
  2. filtrationAfter 21 hours the mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography (Biotage SP4)
  5. washeluting with a gradient of 0 to 100% Et2O in hexane

출처 및 근거

ORD 기록
ord-9e4f8a5d2a2f4b4d9194426256e2f22a
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07956083B2

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