Sodium Carbonate → HCID 69872478, compound

Participants

Reaction Conditions

Reaction Steps

A 50 mL flask was charged with 2-methyl-2-[4-(2-{5-methyl-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-oxazol-4-yl}-ethoxy)-phenoxy]-propionic acid ethyl ester (198 mg, 0.371 mmol), 2-bromopyrimidine (54 mg, 338 mmol), and 5 mL of isopropanol. The flask was purged with N2 three times. After 20 min, palladium acetate (3.0 mg, 0.04 mmol) and triphenylphosphine (3.5 mg, 0.04 mmol) were added. Following addition of a solution of sodium carbonate (43 mg in 1 mL H2O), the mixture was heated to 86° C. for 4 h. The solvent was removed under reduced pressure and the remaining residue taken up in CH2Cl2 (25 mL) and extracted with 0.5 N NaOH (25 mL). The aqueous layer was back extracted with an additional 25 mL CH2Cl2 and the organic layers combined. The organic layer was washed with 1 N NaOH (25 mL) and H2O (25 mL) and then dried and concentrated in vacuo. Flash chromatography provided 45.7 mg (28%) of desired product as a clear oil: 1H NMR (400 MHz, CDCl3) δ8.76 (d, 1 H), 8.45 (d, 2H), 8.06 (d, 2 H), 7.15 (t, 2 H), 6.76 (d, 2 H), 6.71 (d, 2 H), 4.18 (q, 2 H), 4.14 (t, 2 H), 2.93 (t, 2 H), 2.33 (s, 3 H), 1.45 (s, 6 H), 1.21 (t, 3 H); MS (EI) 488.3 (M+H)+.

Provenance & Evidence