3-Methoxypropyne → HCID 178494848, compound

Participants

Reaction Steps

To a suspension of N-(4-chlorobenzyl)-4-hydroxy-2-iodothieno[2,3-b]pyridine-5-carboxamide (Example No. 2) (1.00 g) in diethylamine (28 mL) is added copper iodide (0.128 g), and Pd(PPh3)2Cl2 (0.079 g) followed by addition of propargyl methyl ether (0.27 mL). The reaction is stirred at rt for 18 h. The reaction mixture is partitioned between H2O (100 mL) and CH2Cl2 (100 mL). The organic layer is removed, and the aqueous layer is extracted with CH2Cl2 (3×100 mL). Combined organic layers are washed with a saturated aqueous NH4Cl solution (200 mL), dried with MgSO4, filtered, and concentrated in vacuo. The resulting brown oil is purified via column chromatography (CH2Cl2:CH3OH; 98:2). The resulting impure material is re-purified via column chromatography (heptane:2-propanol, 10:1; CH2Cl2:CH3OH, 98:2). Fractions homogeneous by TLC are combined and concentrated in vacuo to yield to yield 0.260 g (30%) of the title compound as an off-white solid.

Provenance & Evidence