Sodium Fluoride → HCID 53752613, compound

Participants

Reaction Conditions

Reaction Steps

To 250 mg (0.37 mmol) of N-[4-(4-phenylpiperidin-1-yl)-3-tributylstannylbut-2-en-1-yl]-N-methylbenzenesulfonamide from Example 21, Step B (isomeric higher Rf product) in 0.5 mL of N-methylpyrrolidinone under argon was added 75 mg (0.55 mmol) of potassium carbonate, 8 mg (2% cat) of dichlorobis(triphenylphosphine)-palladium (II) and 90 mg (0.55 mmol) of bromobenzene. The mixture was heated at 70° C. for 24 h, cooled, treated with aqueous sodium fluoride for 10 min, and partitioned between water and ether. The water layer was reextracted with ether and each organic layer was washed with brine, dried over sodium sulfate, combined and concentrated in vacuo. The residue was purified by FCC eluting with 20-25% ethyl acetate/hexanes to give 120 mg of title product as an oil. 1H NMR (400 MHz, CDCl3): δ 1.55-1.6 (m, 2H), 2.75 (br d, J=11, 2H), 2.00 (br dt, J=2 and 14, 2H), 2.42 (m, 1H), 2.78 (s, 3H), 2.93 (br d, J=11, 2H), 3.33 (s, 2H), 4.05 (d, J=6.5, 2H), 5.78 (t, J=6.5, 1H), 7.1-7.4 (3 m, 5H), 7.5-7.65 (m, 3H), 7.84 (dd, J=1.5 and 7, 2H). Mass spectrum (ESI): m/z 461 (M+1, 100%).

Provenance & Evidence