반응 #606177

반응 방정식

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

cyclopropyl boronic acid

K2CO3

CH2Cl2

→

3-(7-cyclopropyl-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

수율 39.8%

용매

dioxane

H2O

반응 조건

후처리

1. 1
   기타the solvent was removed in vacuo
2. 2
   기타The residue was purified by preparative HPLC (Table 3, Method 4)

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 (0.080 g, 0.17 mmol), cyclopropyl boronic acid (0.044 g, 0.52 mmol), K2CO3 (0.047 g, 0.34 mmol) and Pd(dppf)Cl2.CH2Cl2 (0.014 g, 0.017 mmol) in dioxane (3 mL) and H2O (0.5 mL) was stirred at 100° C. for 15 h. The mixture was cooled to ambient temperature and the solvent was removed in vacuo. The residue was purified by preparative HPLC (Table 3, Method 4) to give 3-(7-cyclopropyl-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 pale yellow solid (0.029 g, 33%). LC/MS (Table 1, Method 2) Rt=1.228 min.; MS m/z: 429 [M+H]+.

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