Methane → 1-(3-Fluoro-4-hydroxyphenyl)-1H-indazol-4-ol

HRID 2423094노트

반응식

HRID 2423094 반응식
[F:1][C:2]1[CH:3]=[C:4]([N:16]2[C:24]3[C:19](=[C:20]([O:25]CC4C=CC=CC=4)[CH:21]=[CH:22][CH:23]=3)[CH:18]=[N:17]2)[CH:5]=[CH:6][C:7]=1[O:8]CC1C=CC=CC=1.C>C(O)C.C(OCC)(=O)C.C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([N:16]2[C:24]3[CH:23]=[CH:22][CH:21]=[C:20]([OH:25])[C:19]=3[CH:18]=[N:17]2)[CH:5]=[CH:6][C:7]=1[OH:8]

참가 물질

6

반응물 2

HCID 297MethaneHCID 592729821-{3-Fluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indazole

생성물 1

HCID 1359069491-(3-Fluoro-4-hydroxyphenyl)-1H-indazol-4-ol수율 81.5%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매HCID 21584252Ethanol ethylacetate용매

실험 절차

A mixture of 1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indazole (D2) (307 mg) in ethanol/ethyl acetate (˜50 mL, 1:1) was hydrogenated in the presence of 10% Pd on charcoal (150 mg) at atmospheric pressure and room temperature for 3 hrs. The mixture was filtered and concentrated and then chromatographed on silica gel (elution with 0-50% ethyl acetate in hexane) to give an off white solid. This was dissolved in ethyl acetate and stirred with charcoal (Norit SX+, 10 mg) for 30 minutes. The mixture was filtered and concentrated to give the title compound (E1) (144 mg).

후처리

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customchromatographed on silica gel (elution with 0-50% ethyl acetate in hexane)
  4. customto give an off white solid
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d595ae9388a44a5999fdecedb542972d
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960563B2

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