Sodium Carbonate → HCID 86727169, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (197 mg, 0.946 mmol) and 5-(4-bromo-2-chlorophenyl)-1,3,4-thiadiazol-2-amine (250 mg, 0.860 mmol) in dioxane (8 mL) was added Pd(PPh3)4 (50 mg, 0.043 mmol) followed by a solution of Na2CO3 (274 mg, 2.58 mmol) in water (2 mL). The reaction mixture was purged with nitrogen, sealed, and heated at 80° C. for 1 hour under microwave irradiation, then for an additional 2.5 hours at an increased temperature of 120° C. The reaction mixture was diluted with DCM (40 mL) and washed with saturated NaHCO3(aq) (40 mL). A few mLs of saturated NaCl(aq) were added to clear the resulting slight emulsion and the organic phase separated, dried over MgSO4, and filtered. The filtrate was concentrated in vacuo to afford the crude product as a yellow solid. The crude material was pre-absorbed onto silica gel and purified by flash chromatography using a 24 g silica cartridge running a MeOH/DCM gradient to afford the title compound as a pale yellow solid (118 mg, 47% yield). LC-MS: Rt 0.83 min; MS m/z 292.0 [M+H]+ [Method A]. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.31 (s, 1H), 7.97-8.03 (m, 2H), 7.83 (d, J=1.52 Hz, 1H), 7.65 (dd, J=8.34, 1.77 Hz, 1H), 7.41 (s, 2H), 3.87 (s, 3H).

Provenance & Evidence