Trimethylamine → HCID 68865337, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Example 615A (0.446 g, 1.0 mmol), bis(triphenylphosphine))palladium dichloride (35 mg, 0.05 mmol), triphenylphosphine (6.5 mg, 0.025 mmol), 4-hydroxy-1-butyne (0.14 g, 2.0 mmol) and trimethylamine (0.2 mL, 1.5 mmol) in anhydrous THF (6 mL) in a scintillation vial was shaken at ambient temperature for 20 minutes. Copper (I) iodide (5 mg, 0.025 mmol) was added. The mixture was purged with argon, sealed and shaken at 75° C. for 8 hours, treated with ethyl acetate (30 mL), washed with brine (2×10 mL), dried (MgSO4), filtered, and concentrated. The residue was purified on a silica gel column eluting with 30% ethyl acetate in hexanes to provide the desired product, 304 mg, 69.9%. 1H NMR (DMSO-d6) δ 1.11 (t, 3H), 2.55 (q, 2H), 2.61 (t, 2H), 3.63 (t, 2H), 3.73 (s, 3H), 5.25 (t, 1H), 6.86 (d, 1H), 7.25 (d, 1H), 7.32 (t, 1H), 7.52 (d, 2H), 7.82 (dd, 1H), 9.59 (s, 1H); MS (ESI(−)) m/e 434 (M−H)−.

Provenance & Evidence