Potassium Carbonate → HCID 44478735, 화합물

HRID 1971785

반응식

HRID 1971785 반응식
Br[C:2]1[N:3]2[N:9]=[C:8]([O:10][CH3:11])[C:7]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[C:4]2[S:5][CH:6]=1.[C:20]([C:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25](B(O)O)=[C:24]([O:33][CH3:34])[CH:23]=1)#[N:21].C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCCCCCC.C(OCC)(=O)C.C(OCC)(=O)C.O.COCCOC>[C:15]([O:14][C:13](=[O:19])[NH:12][C:7]1[C:8]([O:10][CH3:11])=[N:9][N:3]2[C:2]([C:25]3[C:24]([O:33][CH3:34])=[CH:23][C:22]([C:20]#[N:21])=[CH:27][C:26]=3[O:28][CH3:29])=[CH:6][S:5][C:4]=12)([CH3:18])([CH3:17])[CH3:16]

참가 물질

10

반응물 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 57912433(3-Bromo-6-methoxy-pyrazolo[5,1-b]thiazol-7-yl)-carbamic acid tert-butyl esterHCID 58816649HCID 58816649, 화합물

생성물 1

HCID 44478735HCID 44478735, 화합물수율 51.7%

시약·촉매·용매 5

HCID 167845palladium(II) acetate촉매HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매HCID 21899848Ethylacetate heptane용매

반응 조건

온도
90 °C

실험 절차

To a mixture of tert-butyl (3-bromo-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl)carbamate (461 mg, 1.33 mmol), DME (49 mL) and water (16 mL) were added (4-cyano-2,6-dimethoxyphenyl)boronic acid (412 mg, 2.00 mmol), potassium carbonate (366 mg, 2.66 mmol), triphenylphosphine (174 mg, 0.659 mmol) and palladium acetate (29.8 mg, 0.132 mmol) in that order, and the mixture was stirred at 90° C. (internal temperature) for 2 hours. Water was added to the mixture, and then ethyl acetate was added. After thoroughly shaking the mixture, the organic layer was separated and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and then the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (mixture of n-heptane and ethyl acetate: n-heptane/ethyl acetate=2/1 then 1/1) to obtain the title compound (296 mg, 0.688 mmol).

후처리

  1. stirringAfter thoroughly shaking the mixture
  2. customthe organic layer was separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe mixture was filtered
  6. distillationthe solvent in the filtrate was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (
  8. additionmixture of n-heptane and ethyl acetate

출처 및 근거

ORD 기록
ord-27290163f36f4e06baf6d91a43d803f0
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431603B2

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