Stannane, tributyl(1-ethoxyethenyl)- → 4-(3-chloro-5-(1-ethoxyvinyl)pyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

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A mixture of 4-(3-bromo-5-chloropyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one (0.206 g, 0.441 mmol, Example 11), PdCl2(PPh3)2 (31 mg, 0.044 mmol), tributyl(1-ethoxyvinyl)tin (0.20 mL, 0.57 mmol), and toluene (5 mL) was heated at 80° C. under N2 for 4 h. After allowing to cool to rt, the mixture was filtered through Celite and washed with EtOAc. The filtrate was washed with aqueous KF, dried, filtered, concentrated, and purified by silica gel chromatography (0→50% EtOAc/hexanes) to give 4-(3-chloro-5-(1-ethoxyvinyl)pyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.19 (s, 1H), 8.80 (s, 1H), 8.65 (s, 1H), 7.94 (d, 1H), 7.16 (d, 1H), 4.83 (m, 1H), 4.53 (m, 2H), 4.41 (d, 1H), 3.90 (s, 3H), 3.61 (m, 2H), 1.85-1.52 (m, 8H), 0.89 (t, 3H); MS (ESI): 457.1.

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