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Water → 5-Bromo-1-(3-fluoro-4-hydroxyphenyl)-1H-indazol-4-ol

HRID 2423104
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HRID 2423104 반응식
[Br:1][C:2]1[C:3]([O:26]C)=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][C:14]([O:17]CC3C=CC=CC=3)=[C:13]([F:25])[CH:12]=1)[N:6]=[CH:5]2.B(Br)(Br)Br.O.C(OCC)(=O)C>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([F:25])[CH:12]=3)[N:6]=[CH:5][C:4]=2[C:3]=1[OH:26]
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참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 592729765-Bromo-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-4-(methyloxy)-1H-indazole

생성물 1

HCID 1359103655-Bromo-1-(3-fluoro-4-hydroxyphenyl)-1H-indazol-4-ol수율 74.5%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

A solution of 5-bromo-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-4-(methyloxy)-1H-indazole (D20) (71 mg) in dry dichloromethane (2 mL) was cooled to −78° C. under argon and treated dropwise with boron tribromide solution (0.75 mL of 1M solution in dichloromethane, 0.75 mmol). The mixture was allowed to reach room temperature and was stirred overnight. Water and ethyl acetate were added and the pH of the aqueous layer was adjusted to 7 and the product was extracted into ethyl acetate. The extracts were dried (Na2SO4), concentrated and chromatographed (silica gel, 0-100% ethyl acetate in hexane) to give the title compound (E11) as a beige solid (40 mg)

후처리

  1. customto reach room temperature
  2. extractionthe product was extracted into ethyl acetate
  3. dry with materialThe extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. customchromatographed (silica gel, 0-100% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-4c8adedf33174b289b4e8c5b249e9ffd
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07960563B2

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