Potassium Carbonate → HCID 57912464, 화합물

HRID 1971792

반응식

HRID 1971792 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.[CH:20]1([O:24][CH2:25][C:26]2[CH:31]=[C:30]([O:32][CH3:33])[C:29](B(O)O)=[C:28]([O:37][CH3:38])[CH:27]=2)[CH2:23][CH2:22][CH2:21]1.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.C(OCC)(=O)C.O.COCCOC>[CH:20]1([O:24][CH2:25][C:26]2[CH:27]=[C:28]([O:37][CH3:38])[C:29]([C:2]3[N:3]4[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]4[S:5][CH:6]=3)=[C:30]([O:32][CH3:33])[CH:31]=2)[CH2:23][CH2:22][CH2:21]1

참가 물질

9

반응물 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 57912433(3-Bromo-6-methoxy-pyrazolo[5,1-b]thiazol-7-yl)-carbamic acid tert-butyl esterHCID 57912446{4-[(Cyclobutyloxy)methyl]-2,6-dimethoxyphenyl}boronic acid

생성물 1

HCID 57912464HCID 57912464, 화합물수율 89.4%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

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 (987 mg, 2.83 mmol), DME (80 mL) and water (28 mL) were added {4-[(cyclobutyloxy)methyl]-2,6-dimethoxyphenyl}boronic acid (904 mg, 3.4 mmol), potassium carbonate (785 mg, 5.68 mmol), triphenylphosphine (370 mg, 1.42 mmol) and palladium acetate (63.7 mg, 0.282 mmol) in that order, and the mixture was stirred at 90° C. (internal temperature) for 3 hours. Water was added to the reaction 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) to obtain the title compound (1.24 g, 2.53 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 (mixture of n-heptane and ethyl acetate: n-heptane/ethyl acetate=2/1)

출처 및 근거

ORD 기록
ord-c00b2c3d15a94d3cbcfc301c34f7af67
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431603B2

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