Water → 4-[4-(4-Ethyl-5-fluoro-2-hydroxyphenoxy)-3-fluorobenzoyl]piperazin-2-one

HRID 467541노트

반응식

HRID 467541 반응식
B(Br)(Br)Br.[CH2:5]([C:7]1[C:29]([F:30])=[CH:28][C:10]([O:11][C:12]2[CH:26]=[CH:25][C:15]([C:16]([N:18]3[CH2:23][CH2:22][NH:21][C:20](=[O:24])[CH2:19]3)=[O:17])=[CH:14][C:13]=2[F:27])=[C:9]([O:31]C)[CH:8]=1)[CH3:6].O>ClCCl>[CH2:5]([C:7]1[C:29]([F:30])=[CH:28][C:10]([O:11][C:12]2[CH:26]=[CH:25][C:15]([C:16]([N:18]3[CH2:23][CH2:22][NH:21][C:20](=[O:24])[CH2:19]3)=[O:17])=[CH:14][C:13]=2[F:27])=[C:9]([OH:31])[CH:8]=1)[CH3:6]

참가 물질

5

반응물 3

HCID 962WaterHCID 25134Boron tribromideHCID 671162484-[4-(4-Ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoyl]piperazin-2-one

생성물 1

HCID 513473574-[4-(4-Ethyl-5-fluoro-2-hydroxyphenoxy)-3-fluorobenzoyl]piperazin-2-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A commercial solution of boron tribromide (1N in DCM, 3.5 mL, 3.46 mmol) was added to a solution of 4-[4-(4-ethyl-5-fluoro-2-methoxyphenoxy)-3-fluorobenzoy]piperazin-2-one (which may be prepared in accordance with the experimental described in Example 5, step 1; 500 mg, 1.28 mmol) in dichloromethane (4.3 mL) placed under argon at −30° C. The reaction mixture was stirred at room temperature for 36 hours then diluted by addition of dichloromethane (20 mL) and water (20 mL). After separation, the aqueous layer was extracted with dichloromethane (2×20 mL). The combined organic phases were dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by chromatography on silica gel, using dichloromethane/acetone (80:20) as eluent. The title product was obtained as a beige solid (440 mg, 92%).

후처리

  1. custommay be prepared in accordance with the
  2. customplaced under argon at −30° C
  3. customAfter separation
  4. extractionthe aqueous layer was extracted with dichloromethane (2×20 mL)
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-7382e20a963a4e9a94201c226cc0e270
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623865B2

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