Potassium Carbonate → HCID 57912464, Verbindung

HRID 1971792

Reaktionsgleichung

Reaktionsgleichung von HRID 1971792
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

Komponenten

9

Edukt 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

Produkt 1

HCID 57912464HCID 57912464, VerbindungAusbeute 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittel2×HCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-c00b2c3d15a94d3cbcfc301c34f7af67
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431603B2

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