Potassium Carbonate → HCID 86727510, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-7-trifluoromethyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (Example #107, Step A, 4.87 g, 6.279 mmol), tert-butyl 3-methyl-3-(1-(trifluoromethylsulfonyloxy)vinyl)azetidine-1-carboxylate (Prepared from 1-(tert-butoxycarbonyl)-3-methylazetidine-3-carboxylic acid using the procedure detailed in Preparation #4, Steps A-C, 2.168 g, 6.279 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.513 g, 0.628 mmol) and K2CO3 (1.735 g, 12.554 mmol) in dioxane (48 mL) and water (8 mL) was stirred at 90° C. for 3 h. The reaction mixture was cooled to ambient temperature. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (eluting with 0% to 20% EtOAc in petroleum ether) to give 3-methyl-3-{1-[4-methyl-3-oxo-7-trifluoromethyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-vinyl}-azetidine-1-carboxylic acid tert-butyl ester (1.214 g, 31%). LC/MS (Table 1, Method 27) Rt=1.481 min; MS m/z: 633 [M+Na]+.

Provenance & Evidence