Sodium Carbonate → HCID 86727495, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-4-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (Preparation #11, Step E, 2 g, 5.83 mmol), 3-methyl-3-(1-trifluoromethanesulfonyloxy-vinyl)-azetidine-1-carboxylic acid tert-butyl ester (Preparation #20 3.02 g, 8.74 mmol), Na2CO3 (1.235 g, 11.66 mmol) and Pd(Ph3P)4 (3.37 g, 2.91 mmol) in dioxane (20 mL) and water (5 mL) was stirred at 90° C. overnight. 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 0-30% EtOAc in petroleum ether) to give 3-methyl-3-[1-((R)-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl)-vinyl]-azetidine-1-carboxylic acid tert-butyl ester (0.610 g, 25%) as a solid. LC/MS (Table 1, Method 25) Rt=0.867 min.; MS m/z: 413 [M+H]+ and 357 [M+H−56]+. 1H NMR (CDCl3, 400 MHz): δ 8.10 (br. s., 1H), 6.98 (d, J=8.4 Hz, 1H), 6.83 (d, J=8.4 Hz, 1H), 6.78 (s, 1H), 5.33 (s, 1H), 5.10 (s, 1H), 4.74 (m, 1H), 4.67-4.56 (d, J=15.2 Hz, 2H), 4.11 (m, 2H), 3.79 (m, 2H), 1.61 (d, J=15.2 Hz, 3H), 1.55 (m, 3H). 1.46 (s, 9H).

Provenance & Evidence