1,2-Dimethoxyethane → HCID 54689926, compound

Participants

Reaction Conditions

Reaction Steps

3-[4-Bromo-5-(3-methoxy-prop-1-ynyl)-thiophen-2-yl]-4-hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile (75 mg, 0.18 mmol, Example 183) was dissolved in 2 mL of 1:1 DMF:DME and at rt, vinyl tributyltin (0.2 mmol) was added. The reaction vessel was flushed with N2, capped and heated to 100° C. for 2 h. The reaction mixture was filtered and filtered again through a plug of silica gel. The residue was taken up in 1:1 MeOH : DMSO, filtered and purified by RP-HPLC to provide the title compound. MS (ESI) m/z 367.0 (M−H+); 1H NMR (300 MHz, DMSO-d6) δ ppm 7.67 (s, 1H), 7.44 (s, 1H), 7.04 (s, 1H), 6.98 (s, 1H), 6.83 (dd, 1H), 5.83 (d, 1H), 5.30 (d, 1H), 4.38 (d, 2H), 4.38 (app d, 2H), 3.43 (app d, 3H).

Provenance & Evidence