Butyl vinyl ether → HCID 68845177, compound

Participants

Reaction Steps

15.5 g (47.5 mmol) of 1,1,1-Trifluoro-methanesulfonic acid 8-fluoro-6-methoxy-quinolin-4-yl ester, 24.5 mL (0.19 mol) of butyl vinyl ether and 13.3 mL of triethylamine were takent up in 100 mL of DMF. 2.0 g (4.75 mmol) of dppp (1,3-bis(diphenylphosphino)propane) and 1.06 g (4.75 mmol) of Pd(OAc)2 were added and the contents heated to 60 C for 4 hrs. No starting material remained. Contents were rotary-evaporated to remove as much DMF as possible. Crude material was purified by flash chromatography on silica gel using 10% ethyl acetate/hexanes as the eluent to give 9.0 g (69%) of the desired product. 1H NMR (CDCl3, 400 MHz) 8.78 (d, 1H), 7.43 (d, 1H), 7.28 (m, 1H), 7.09 (d, 1H), 4.58 (d, 1H), 4.50 (d, 1H), 3.96 (t, 2H), 3.90 (s, 3H), 1.80 (m, 2H), 1.53 (m, 2H), 0.97 (t, 3H LCMS (M+H)+ 276.

Provenance & Evidence