تفاعل #69549

معادلة التفاعل

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

المردود 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

المردود 91.3%

المذيبات

ethanol

ethyl acetate

Water

ظروف التفاعل

المعالجة

1. 1
   أخرىsynthesized by the method
2. 2
   أخرىthe 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
   ترشيحwere filtered off
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   أخرىThe residue was purified by medium pressure silica gel column chromatography (n-heptane/ethyl acetate

الإجراء التجريبي

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.

المصدر