Cesium carbonate → 4-chloro-6-(1-(methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 527997노트

반응식

HRID 527997 반응식
[Cl:1][C:2]1[C:3]2[CH:10]=[C:9](I)[N:8]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:4]=2[N:5]=[CH:6][N:7]=1.O1CCCC1.O.[CH3:27][S:28]([N:31]1[CH2:36][CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH2:33][CH2:32]1)(=[O:30])=[O:29].C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C>[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([C:34]3[CH2:35][CH2:36][N:31]([S:28]([CH3:27])(=[O:30])=[O:29])[CH2:32][CH:33]=3)[N:8]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:4]=2[N:5]=[CH:6][N:7]=1

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 21881883Oxolane--water (1/1)HCID 574158854-Chloro-6-iodo-7-phenylsulfonyl-7H-pyrrolo[2,3-D]pyrimidineHCID 679734971-Methanesulfonyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine

생성물 1

HCID 904181484-chloro-6-(1-(methylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

To a solution of 4-chloro-6-iodo-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (1.9 g, 4.53 mmol) in 6:1 tetrahydrofuran/water (60 mL) was added 1-(methylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine (1.56 g, 5.43 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (0.37 g, 0.453 mmol) and cesium carbonate (3.54 g, 10.87 mmol). The mixture was heated at 50° C. overnight, cooled and diluted with 50 mL ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, water, and brine, dried over magnesium sulfate, filtered, and concentrated. Purification by flash chromatography on silica (Analogix 280) eluting with a gradient of 10% to 60% ethyl acetate/hexanes gave the title compound. MS (ESI+) m/z 452.5 (M)+.

후처리

  1. temperaturecooled
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate, water, and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography on silica (Analogix 280)
  7. washeluting with a gradient of 10% to 60% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-2dad17fa01554ee489278255ef58a71f
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346813B2

반응 노트

불러오는 중…