alpha-Ethynylbenzenemethanol → HCID 10238395, compound

Participants

Reaction Steps

2-Bromo-N-(4-chlorobenzyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]-pyridine-5-carboxamide (Example 79, 0.593 g) was suspended in a mixture of triethylamine (15 mL) and DMF (3 mL). CuI (0.029 g), Pd(PPh3)2Cl2 (0.105 g), and then 1-phenyl-2-propyn-1-ol (0.36 mL) were added. The reaction mixture was stirred at room temperature for 30 min and then was partitioned between CH2Cl2 (50 mL) and water (50 mL). The aqueous layer was separated and then extracted with CH2Cl2 (3×50 mL). The combined organic layers were washed with a sat. aq. ammonium chloride solution (100 mL), dried (MgSO4), filtered, and concentrated in vacuo. The resulting solid was purified by column chromatography (CH2Cl2/methanol; 99/1, 98/2) followed by recrystallization from methanol to yield 0.260 g of the title compound as a yellow solid. Physical characteristics. M.p. 209-211° C. (dec); 1H NMR (400 MHz, DMSO-d6) δ 10.48, 8.60, 7.53-7.51, 7.43-7.32, 6.43, 5.73, 4.55, 3.91; MS (ESI+) m/z 447 (M+H)+.

Provenance & Evidence