Cesium carbonate → Tert-Butyl 4-[2-(4-methanesulfonylbenzoylamino)-pyridin-5-yl]-3,6-dihydro-2H-pyridine-1-carboxylate

HRID 42138

반응식

HRID 42138 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:29]2[CH2:30][CH2:31][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:33][CH:34]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[CH3:19][S:16]([C:13]1[CH:14]=[CH:15][C:10]([C:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([C:29]3[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH:30]=3)=[CH:7][N:6]=2)=[O:20])=[CH:11][CH:12]=1)(=[O:18])=[O:17]

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 60650971N-(5-Bromopyridin-2-yl)-4-methanesulfonylbenzamide

생성물 1

HCID 67083258Tert-Butyl 4-[2-(4-methanesulfonylbenzoylamino)-pyridin-5-yl]-3,6-dihydro-2H-pyridine-1-carboxylate수율 22.4%

시약·촉매·용매 3

HCID 178477754HCID 178477754, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

To a solution of N-(5-bromopyridin-2-yl)-4-methanesulfonylbenzamide (287 mg, 0.81 mmol) and tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate (305 mg, 0.97 mmol) in dry N,N-dimethylformamide (10 mL) was added [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (complex with dichloromethane) (33 mg, 0.040 mmol) and cesium carbonate (527 mg, 1.6 mmol). The mixture was stirred at 90° C. overnight under N2, allowed to cool to room temperature, diluted with water (10 mL) and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2) to give the title compound as a white crystal (83 mg, yield 22%).

후처리

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2)

출처 및 근거

ORD 기록
ord-f4e9a30a2210477b8a0084f312a4c427
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536176B2

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