Boron tribromide → 1-(4-{4-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-yl]-imidazol-1-yl}-phenyl)-ethanone

HRID 2219414노트

반응식

HRID 2219414 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[N:14]=[CH:15][N:16]([C:18]4[CH:23]=[CH:22][C:21]([C:24](=[O:26])[CH3:25])=[CH:20][CH:19]=4)[CH:17]=3)=[C:11]([CH2:27][O:28]C)[O:10][N:9]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[N:14]=[CH:15][N:16]([C:18]4[CH:23]=[CH:22][C:21]([C:24](=[O:26])[CH3:25])=[CH:20][CH:19]=4)[CH:17]=3)=[C:11]([CH2:27][OH:28])[O:10][N:9]=2)=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 67420992HCID 67420992, 화합물

생성물 1

HCID 674206471-(4-{4-[3-(4-Fluoro-phenyl)-5-hydroxymethyl-isoxazol-4-yl]-imidazol-1-yl}-phenyl)-ethanone수율 15.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

To a stirred solution of 1-(4-{4-[3-(4-fluoro-phenyl)-5-methoxymethyl-isoxazol-4-yl]-imidazol-1-yl}-phenyl)-ethanone (239 mg, 0.61 mmol) in dry dichloromethane (4 mL) was added slowly boron tribromide (0.17 mL, 0.3 mmol) at dry ice-acetone bath cooling temperature. After complete addition, the resulting mixture was stirred at −78° C. for 15 min, and −15° C. for 35 min, and then allowed to warm up to room temperature for 20 min. The reaction was quenched with saturated sodium bicarbonate (30 mL). The organic layer was separated, and the aqueous phase was extracted with dichloromethane and ethylacetate. The combined organic extracts were then dried over sodium sulphate and evaporated. Purification by preparative HPLC afforded the title compound (35 mg, 15%) which was obtained as an off-white solid. MS: m/e=378.0 [M+H]+.

후처리

  1. temperaturecooling temperature
  2. additionAfter complete addition
  3. wait−15° C. for 35 min
  4. temperatureto warm up to room temperature for 20 min
  5. customThe reaction was quenched with saturated sodium bicarbonate (30 mL)
  6. customThe organic layer was separated
  7. extractionthe aqueous phase was extracted with dichloromethane and ethylacetate
  8. dry with materialThe combined organic extracts were then dried over sodium sulphate
  9. customevaporated
  10. customPurification by preparative HPLC

출처 및 근거

ORD 기록
ord-90c04bd604cd43ea968769424e82795e
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07414061B2

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