Cesium carbonate → HCID 44556110, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 5-[3-(propan-2-yl)phenyl][1,2,4]triazolo[1,5-a]pyridin-2-amine (88.9 mg, 0.352 mmol, 1.00 equiv), 4-chloro-2-methylpyridine (53.9 mg, 0.423 mmol, 1.20 equiv), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (17.6 mg, 0.0369 mmol, 0.105 equiv), cesium carbonate (237 mg, 0.727 mmol, 2.06 equiv), and tris(dibenzylideneacetone)dipalladium(0) (10.0 mg, 0.0109 mmol, 0.0310 equiv) in N,N-dimethylformamide (2 mL) was heated in the microwave to 210° C. for 20 min. The reaction mixture was concentrated in vacuo (˜1 mm Hg). The resulting residue was partitioned between saturated aqueous sodium chloride solution (5 mL) and ethyl acetate (5 mL). The organic was separated, and the aqueous phase was extracted with ethyl acetate (2×5 mL). The collected organic was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by preparative HPLC yielded a white solid (65.5 mg, 54%). 1H NMR (400 MHz, DMSO-d6), δ: 10.13 (s, 1H), 8.16 (m, 1H), 7.95 (s, 1H), 7.83 (m, 1H), 7.63-7.72 (m, 2H), 7.44-7.55 (m, 4H), 7.25 (dd, J=7.1, 1.3 Hz, 1H), 3.03 (m, 1H), 2.37 (s, 3H), 1.30 (d, J=6.9 Hz, 6H).

Provenance & Evidence