Hydrochloric Acid → 2-(6-Bromoquinolin-2-yl)-1,1,1-trifluoropropan-2-ol

HRID 1693072

반응식

HRID 1693072 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12](=[O:14])[CH3:13])[CH:6]=[CH:5]2.[F:15][C:16]([Si](C)(C)C)([F:18])[F:17].Cl>[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([OH:14])([CH3:13])[C:16]([F:18])([F:17])[F:15])[CH:6]=[CH:5]2

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 574581651-(6-Bromoquinolin-2-yl)ethanone

생성물 1

HCID 574581662-(6-Bromoquinolin-2-yl)-1,1,1-trifluoropropan-2-ol수율 105.1%

시약·촉매·용매 2

HCID 2724141Tetrabutylammonium Fluoride촉매HCID 6228Dimethylformamide용매

실험 절차

A DMF (5 ml) solution of 1-(6-bromoquinolin-2-yl)ethanone (129 mg, 0.52 mmol), (trifluoromethyl)trimethylsilane (220 mg, 1.55 mmol) and tetrabutylammonium fluoride (13.5 mg, 0.052 mmol) was stirred at 100° C. for 2 hours. Then the mixture was cooled to room temperature and 1N-hydrochloride aqueous solution (2 ml) was added. After 4 hours, the mixture was quenched with saturated sodium bicarbonate aqueous solution, and the product was extracted with ethyl acetate which was dried over sodium sulfate. Then, filtration, evaporation and purification through silica gel column chromatography, eluting with hexane/ethyl acetate (4:1), furnished the title compound (175 mg, quant.) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.81 (3H, s), 6.51 (1H, s), 7.64 (1H, d, J=8.1 Hz), 7.66-7.89 (1H, m), 8.00-8.12 (2H, m), 8.21 (1H, d, J=8.8 Hz). MS (ESI): m/z 320, 322 (M+H)+.

후처리

  1. customthe mixture was quenched with saturated sodium bicarbonate aqueous solution
  2. extractionthe product was extracted with ethyl acetate which
  3. dry with materialwas dried over sodium sulfate
  4. filtrationThen, filtration, evaporation and purification through silica gel column chromatography
  5. washeluting with hexane/ethyl acetate (4:1)

출처 및 근거

ORD 기록
ord-28786fdef50f42f7923fb0988b47e921
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158650B2

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