반응 #606179

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3-(7-bromo-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yloxy)-azetidine-1-carboxylic acid tert-butyl ester

isopropenyl boronic acid

K2CO3

CH2Cl2

→

3-(7-isopropenyl-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yloxy)-azetidine-1-carboxylic acid tert-butyl ester

용매

dioxane

H2O

반응 조건

후처리

1. 1
   기타the solvent was removed in vacuo
2. 2
   기타The residue was purified by preparative TLC (eluting with 20% EtOAc in petroleum ether)

실험 절차

A mixture of 3-(7-bromo-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yloxy)-azetidine-1-carboxylic acid tert-butyl ester (Example #65, Step G, 0.030 g, 0.064 mmol), isopropenyl boronic acid (0.032 g, 0.193 mmol), K2CO3 (0.018 g, 0.13 mmol) and Pd(dppf)Cl2.CH2Cl2 (0.011 g, 0.013 mmol) in dioxane (3 mL) and H2O (0.5 mL) was stirred at 80° C. for 15 h. The mixture was cooled to ambient temperature and the solvent was removed in vacuo. The residue was purified by preparative TLC (eluting with 20% EtOAc in petroleum ether) to give 3-(7-isopropenyl-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yloxy)-azetidine-1-carboxylic acid tert-butyl ester as a white solid (0.09 g, 33%). LC/MS (Table 1, Method 2) Rt=1.241 min.; MS m/z: 429 [M+H]+.

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