反应 #69552

ord-d3ce3cfeb8994b038d83d377dfc543e2

反应方程式

C1COCCO1
dioxane
COCc1cc(OC)c(-c2c(Br)sc3c(NC(=O)OC(C)(C)C)c(OC)nn23)c(OC)c1
tert-butyl{2-bromo-3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl}carbamate
C[CH2][Zn][CH2]C
diethyl zinc
CCc1sc2c(NC(=O)OC(C)(C)C)c(COC)nn2c1-c1c(OC)cc(COC)cc1OC
title compound
CCc1sc2c(NC(=O)OC(C)(C)C)c(COC)nn2c1-c1c(OC)cc(COC)cc1OC
tert-Butyl{3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-ethyl-6-methoxymethylpyrazolo[5,1-b][1,3]thiazol-7-yl}carbamate

反应条件

温度
60°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    workup.DISTILLATIONthe solvent was directly distilled off under reduced pressure
  2. 2
    其他The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

实验过程

To a dioxane (5 mL) solution of tert-butyl{2-bromo-3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl}carbamate (118 mg, 0.224 mmol), 1M diethyl zinc (0.448 mL, 0.448 mmol) and bis(tri-tert-butylphosphine)palladium(0) (5.70 mg, 0.011 mmol) were added, and the mixture was heated at 60° C. for one hour. After the reaction was completed, the solvent was directly distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=1/1) to obtain the title compound (84 mg, 0.176 mmol).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08530504B2uspto-grants-2013_09