Cesium carbonate → HCID 58368449, 화합물

HRID 1192596노트

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HRID 1192596 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@H:25]1[CH2:29][CH2:28][NH:27][CH2:26]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.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>[Cl:17][C:10]1[CH:9]=[C:8]([C:18](=[O:20])[CH3:19])[C:7]([N:27]2[CH2:28][CH2:29][C@H:25]([F:24])[CH2:26]2)=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[N:15]2

참가 물질

8

반응물 3

HCID 10796Cesium carbonateHCID 16217739(s)-3-Fluoropyrrolidine hydrochlorideHCID 58368658HCID 58368658, 화합물

생성물 1

HCID 58368449HCID 58368449, 화합물수율 100.5%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 634876Binap, (A+-)-촉매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

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온도
65 °C

실험 절차

A stirred mixture of 7-acetyl-5-chloroquinolin-8-yl trifluoromethanesulfonate (0.12 g, 0.34 mmol, from Example 47, Step 2), (3S)-3-fluoropyrrolidine hydrochloride (0.051 g, 0.41 mmol), palladium acetate (1.5 mg, 0.0068 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (6.3 mg, 0.010 mmol) and cesium carbonate (0.31 g, 0.95 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 MgSO4 and evaporated to dryness. The resulting residue was purified on silica gel (eluting with 0 to 30% ethyl acetate in hexane) to give the desired product (0.10 g). LCMS calculated for C15H15ClFN2O (M+H)+: m/z=293.1; Found: 293.0.

후처리

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washThe filtrate was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe resulting residue was purified on silica gel (eluting with 0 to 30% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-db17f7d539d9482d9d97c63a65720db4
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680108B2

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