Potassium Carbonate → Tert-butyl[3-(4-hydroxy-2,6-dimethoxyphenyl)-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl]carbamate

HRID 41277Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 41277
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[C:9]([O:17][CH3:18])=[N:10][N:11]2[C:15](Br)=[CH:14][S:13][C:12]=12)([CH3:4])([CH3:3])[CH3:2].[Si]([O:27][C:28]1[CH:33]=[C:32]([O:34][CH3:35])[C:31](B(O)O)=[C:30]([O:39][CH3:40])[CH:29]=1)(C(C)(C)C)(C)C.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[C:9]([O:17][CH3:18])=[N:10][N:11]2[C:15]([C:31]3[C:30]([O:39][CH3:40])=[CH:29][C:28]([OH:27])=[CH:33][C:32]=3[O:34][CH3:35])=[CH:14][S:13][C:12]=12)([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 57912433(3-Bromo-6-methoxy-pyrazolo[5,1-b]thiazol-7-yl)-carbamic acid tert-butyl esterHCID 57912460(4-{[tert-Butyl(dimethyl)silyl]oxy}-2,6-dimethoxyphenyl)boronic acid

Produkt 1

HCID 44479005Tert-butyl[3-(4-hydroxy-2,6-dimethoxyphenyl)-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl]carbamateAusbeute 53,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of tert-butyl(3-bromo-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl)carbamate (375 mg, 1.08 mmol) in 1,4-dioxane (25 ml) and water (12.5 ml) were added (4-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethoxyphenyl)boronic acid (505 mg, 1.61 mmol), tetrakis(triphenylphosphine)palladium(0) (125 mg, 0.108 mmol) and potassium carbonate (298 mg, 2.15 mmol), and the mixture was heated to reflux at 110° C. for two hours and 35 minutes. The reaction mixture was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by medium pressure silica gel column chromatography (n-heptane/ethyl acetate=10% then 70%) to obtain the title compound (242 mg, 0.574 mmol).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by medium pressure silica gel column chromatography (n-heptane/ethyl acetate=10%

Quellen und Nachweise

ORD-Eintrag
ord-d798f18f0e5e4add9c03c4fdaad65d89
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530504B2

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