Cesium carbonate → 1-[5-Chloro-8-(4,4-difluoropiperidin-1-yl)quinolin-7-yl]ethanone

HRID 1192551노트

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HRID 1192551 반응식
FC(F)(F)S(O[C:7]1[C:8]([C:18](=[O:20])[CH3:19])=[CH:9][C:10]([Cl:17])=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[CH:12]2)(=O)=O.Cl.[F:24][C:25]1([F:31])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:17][C:10]1[CH:9]=[C:8]([C:18](=[O:20])[CH3:19])[C:7]([N:28]2[CH2:29][CH2:30][C:25]([F:31])([F:24])[CH2:26][CH2:27]2)=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[N:15]2

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 27583514,4-Difluoropiperidine hydrochlorideHCID 58368658HCID 58368658, 화합물

생성물 1

HCID 583685421-[5-Chloro-8-(4,4-difluoropiperidin-1-yl)quinolin-7-yl]ethanone

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

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온도
65 °C

실험 절차

A stirred mixture of 7-acetyl-5-chloroquinolin-8-yl trifluoromethanesulfonate (0.106 g, 0.301 mmol), 4,4-difluoropiperidine hydrochloride (0.0570 g, 0.362 mmol), palladium acetate (1 mg, 0.006 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (6 mg, 0.009 mmol), and cesium carbonate (0.274 g, 0.843 mmol) in tetrahydrofuran (3 mL) was heated at 65° C. overnight. The mixture was cooled, diluted with dichloromethane and filtered. The filtrate was washed with brine, dried over sodium sulfate and evaporated to dryness. The resulting residue was purified on silica gel, eluting with 0 to 50% ethyl acetate in hexane, to give the desired product. LCMS calculated for C16H16ClF2N2O (M+H)+: m/z=325.1; Found: 325.0.

후처리

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washThe filtrate was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customThe resulting residue was purified on silica gel
  7. washeluting with 0 to 50% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-f5ea403c5a8f4aa2b2404dc0385ba3c7
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680108B2

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