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

HRID 2423094ノート

反応式

HRID 2423094 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒HCID 21584252Ethanol ethylacetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d595ae9388a44a5999fdecedb542972d
出典データセット
uspto-grants-2011_06
特許番号
US07960563B2

反応ノート

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