HCID 11089657, compound → HCID 86599498, compound

Participants

Reaction Steps

A mixture of ethyl 8-iodo-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in Example 21a, Step 2 (01597/1 PR) (10.6 g, 21.9 mmole), crude tributyl(ethoxyethynyl)stannane prepared as in Step 1 (10.4 g, 28.5 mmole assumed), triethylammonium chloride (3.63 g, 21.9 mmole) and Pd (PPh3)2 (0.769 g, 1.10 mmole) in DMF (140 mL) was stirred at room temperature overnight. The mixture was hen diluted with H2O and extracted with ethyl ether (2×200 mL). The combined extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Purification by silica chromatography (5%-6.5% EtOAc:hexanes gradient) gave 4.06 g (44% yield) of the product as a yellow crystalline solid: 1H NMR (dmso-d6/300 MHz) 7.95 (s, 1H), 7.55 (d, 1H, J=2.0 Hz), 7.37 (d, 1H, J=2.2 Hz), 6.11 (q, 1H, J=7.3 Hz), 4.32-4.20 (m, 4H), 1.39 (t, 3H, J=7.1 Hz), 1.26 (t, 3H, J=7.2 Hz).

Provenance & Evidence