Sodium Carbonate → HCID 69871063, 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), 5-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 the desired product. 1H NMR (400 MHz, CDCl3) δ9.23 (s, 1H), 9.20 (s, 2H), 8.16 (d, 2H), 7.65 (d, 2H), 6.88 (d, 2H), 6.75 (d, 2H), 4.21 (q, 2H), 4.20 (t, 2H), 3.00 (t, 2H), 2.39 (s, 3H), 1.48 (s, 6H), 1.21 (t, 3H); MS (EI) 4.88.1 (M+H)+.

Provenance & Evidence