Potassium Carbonate → methyl 2-(acetylamino)-3-(4-{3-[(tert-butoxycarbonyl)amino]-1-methyl-1H-pyrazol-4-yl}phenyl)propanoate

HRID 425395노트

반응식

HRID 425395 반응식
[C:1]([NH:4][CH:5]([CH2:10][C:11]1[CH:16]=[CH:15][C:14](B2OC(C)(C)C(C)(C)O2)=[CH:13][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[C:33]1[C:34]([NH:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[N:35][N:36]([CH3:38])[CH:37]=1>CN(C)C=O.O>[C:1]([NH:4][CH:5]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:33]2[C:34]([NH:39][C:40]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:46])=[N:35][N:36]([CH3:38])[CH:37]=2)=[CH:15][CH:16]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 66705669Methyl 2-(acetylamino)-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoateHCID 86637803tert-butyl (4-bromo-1-methyl-1H-pyrazol-3-yl)carbamate

생성물 1

HCID 66705663methyl 2-(acetylamino)-3-(4-{3-[(tert-butoxycarbonyl)amino]-1-methyl-1H-pyrazol-4-yl}phenyl)propanoate

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
85 °C

실험 절차

1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (353 mg, 0.43 mmol) was added to a degassed, ambient temperature solution of methyl 2-(acetylamino)-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate (1.5 g, 4.3 mmol), potassium carbonate (2.39 g, 17.3 mmol) and tert-butyl (4-bromo-1-methyl-1H-pyrazol-3-yl)carbamate (1.19 g, 4.3 mmol) in wet N,N-dimethylformamide (40 mL). After stirring at 85° C. overnight, the reaction mixture was cooled, diluted with water and extracted with methylene chloride and ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% acetone/methylene chloride afforded methyl 2-(acetylamino)-3-(4-{3-[(tert-butoxycarbonyl)amino]-1-methyl-1H-pyrazo 1-4-yl}phenyl)propanoate.

후처리

  1. temperaturethe reaction mixture was cooled
  2. extractionextracted with methylene chloride and ethyl acetate
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ec7cf2c7002f4edba27d951528c821a5
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106070B2

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