4-Bromo-3,5-dimethylpyridine → 8-(cyclopentyloxy)-4-(3,5-dimethylpyridin-4-ylamino)-7-methoxy-2H-chromen-2-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-amino-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one (0.176 g, 0.640 mmol, Example 3, Step 1), 4-bromo-3,5-dimethylpyridine (0.108 g, 0.580 mmol), Pd2(dba)3 (55 mg, 0.06 mmol), 2,2-dicyclohexylphosphorane triisopropylbiphenyl (55 mg, 0.12 mmol), sodium tert-butoxide (67 mg, 0.69 mmol), and dry toluene (3 mL) was heated to 110° C. under N2 for 2 h. The mixture was allowed to cool to rt, filtered through Celite, washed with EtOAc, concentrated, and purified by reverse-phase HPLC (20→100% acetonitrile:water) to give 8-(cyclopentyloxy)-4-(3,5-dimethylpyridin-4-ylamino)-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.10 (s, 1H), 8.43 (s, 2H), 7.93 (d, 1H), 7.17 (d, 1H), 4.83 (m, 1H), 4.29 (s, 1H), 3.90 (s, 3H), 2.15 (s, 6H) 1.86-1.53 (m, 8H); MS (ESI): 380.9.

Provenance & Evidence