Cesium carbonate → tert-butyl 4-(4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 871092노트

반응식

HRID 871092 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C(C)(C)OB([C:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH:16]=2)O1.[Cl:29][C:30]1[C:31]2[CH:38]=[C:37](I)[N:36]([S:40]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)(=[O:42])=[O:41])[C:32]=2[N:33]=[CH:34][N:35]=1>O1CCCC1.O.C(OCC)(=O)C>[Cl:29][C:30]1[C:31]2[CH:38]=[C:37]([C:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[CH2:17][CH:16]=3)[N:36]([S:40]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)(=[O:42])=[O:41])[C:32]=2[N:33]=[CH:34][N:35]=1

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 574158854-Chloro-6-iodo-7-phenylsulfonyl-7H-pyrrolo[2,3-D]pyrimidine

생성물 1

HCID 58709981tert-butyl 4-(4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
65 °C

실험 절차

A mixture of cesium carbonate (7.45 g, 22.88 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.778 g, 0.95 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (3.98 g, 12.87 mmol), and 4-chloro-6-iodo-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (5 g, 9.53 mmol) in tetrahydrofuran (50 mL) and water (8.33 mL) was heated at 65° C. for 16 hours, diluted with ethyl acetate and washed with water and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica (IntelliFlash Varian 971-FP), eluting with a gradient of 5-80% ethyl acetate in heptanes to provide the title compound. ESI MS: 497.1 (M+Na)+.

후처리

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica (IntelliFlash Varian 971-FP)
  6. washeluting with a gradient of 5-80% ethyl acetate in heptanes

출처 및 근거

ORD 기록
ord-e5a01929a295416893fe28397bcf7091
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969375B2

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