Sodium Carbonate → HCID 57598244, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (5-bromo-1,3,4-thiadiazol-2-yl)methanol (1.2 g, 6.15 mmol) in toluene (40 ml) and ethanol (40 ml) was added 4-fluorophenyl boronic acid (1.03 g, 7.38 mmol) and 2 M aqueous Na2CO3. The reaction mixture was degassed with argon, Pd(PPh3)4 (0.354 g, 0.355 mmol) was added, the reaction mixture was degassed again with argon for 10 min, and then heated to 100° C. for 2 h. The reaction mixture was evaporated under vacuum to remove ethanol, the reaction mixture was diluted with water (50 mL), and extracted with ethyl acetate (200 mL). The organic extracts were dried over sodium sulphate, filtered and evaporated under reduced pressure to obtain crude product. The crude product was purified by Biotage Isolera® One column (using 30% ethyl acetate and hexane) to give (5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl)methanol as a pale yellow solid (0.85 g, 65% yield); LC-MS m/z calcd for [M+H]+ 211.03. found 211.1

Provenance & Evidence