2-Methyl-3-butyn-2-ol → HCID 50915296, compound

Participants

Reaction Conditions

Reaction Steps

A 5 mL microwave vial was charged with a magnetic stir bar, 6-bromo-4-(tetrahydro-2H-pyran-4-ylmethoxy)-3-(thiophen-2-yl)quinolin-2(1H)-one (22 mg, 52 mop, copper(I) iodide (1.0 mg, 5.0 mop, and bis(tri-t-butylphosphine) palladium(0) (1.0 mg, 3.0 μmol). The vessel was sealed. The contents of the vessel were dried under high vacuum, and flushed with nitrogen. Acetonitrile (500 μL) was added under nitrogen followed by addition of 2-methyl-3-butyn-2-ol (18 mg, 210 μmol), and diisopropylethyl amine (46 μL, 260 μmol). The reaction was heated to 100° C. in an oil bath for 3 h. The crude product was purified by reverse-phase chromatography to yield 4-(tetrahydro-2H-pyran-4-ylmethoxy)-6-(3-hydroxy-3-methylbut-1-yn-1-yl)-3-(thiophen-2-yl)quinolin-2(1H)-one as off white solid. LCMS (M+H)=423.9. 1H NMR (400 MHz, CDCl3) 11.0 (s, 1H), 7.90 (s, 1H), 7.84 (d, 1H), 7.52 (m, 2H), 7.24 (1H), 7.18 (t, 1H), 4.00 (dd, 2H) 3.65 (d, 2H), 3.45 (t, 2H), 2.15 (m, 1H), 1.75 (d, 2H), 1.65 (s, 6H), 1.50-1.40 (m, 3H).

Provenance & Evidence