반응 #69549

반응 방정식

tert-butyl[3-bromo-6-methyl-2-(methylthio)pyrazolo[5,1-b][1,3]thiazol-7-yl]carbamate

toluene

sodium carbonate

2,6-dimethoxy-4-(methoxymethyl)phenylboric acid

→

title compound

수율 91.3%

tert-Butyl[3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-6-methyl-2-(methylthio)pyrazolo[5,1-b][1,3]thiazol-7-yl]carbamate

수율 91.3%

용매

ethanol

ethyl acetate

Water

반응 조건

후처리

1. 1
   기타synthesized by the method
2. 2
   기타the organic layer was separated
3. 3
   workup.STIRRINGthe organic layer was stirred at 75° C. for five hours
4. 4
   workup.ADDITIONChloroform was added to the reaction mixture, insoluble matters
5. 5
   여과were filtered off
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   기타The residue was purified by medium pressure silica gel column chromatography (n-heptane/ethyl acetate

실험 절차

To a mixture of tert-butyl[3-bromo-6-methyl-2-(methylthio)pyrazolo[5,1-b][1,3]thiazol-7-yl]carbamate (397 mg, 1.03 mmol), toluene (6.8 mL) and ethanol (3.4 mL) were added 2,6-dimethoxy-4-(methoxymethyl)phenylboric acid (349 mg, 1.55 mmol) synthesized by the method described in WO2004/037822, a 1M aqueous solution of sodium carbonate (2.06 mL, 2.06 mmol) and tetrakis(triphenylphosphine)palladium (119 mg, 0.10 mmol) in this order, and the mixture was heated to reflux at 110° C. for three 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 stirred at 75° C. for five hours. Chloroform was added to the reaction mixture, insoluble matters were filtered off, 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: 33% then 66%) to obtain 450.9 mg (0.94 mmol) of the title compound.

출처