Triethylamine → HCID 22872639, compound

Participants

Reaction Steps

A mixture of 3-(1-BOC-2-(S)-pyrrolidinylmethoxy)-chloro-6-chloropyridine from Example 69a (400 mg, 1.02 mmol), 1-octyne (0.23 mL, 1.54 mmol), Pd(PPh)3Cl2 (36 mg), CuI (catalytic amount) and NEt3 (2.5 mL) in CH2Cl2 (8 mL) was heated at reflux for 16 h. Heating was continued until no starting material remained. The solvent was removed, and the residue was washed with 10% NaOH then extracted with CH2Cl2. The organic extract was dried (MgSO4) and concentrated. The residue was chromatographed (silica gel; hexane:EtOAc, 3:1) to afford the title compound (335 mg, 72% yield): 1H NMR (CDCl3, 300 MHz) δ 0.91 (t, J=7.5 Hz, 3H), 1.23-1.40 (m, 4H), 1.48 (s, 9H), 1.56-1.69 (m, 2H), 1.81-2.06 (m, 5H), 2.46 (t, J=7.5 Hz, 2H), 3.27-3.47 (m, 2H), 3.98-4.21 (m, 4H), 7.29 (br, s, 1H), 7.98 (d, J=3.0 Hz, 1H); MS (CI/NH3) m/z 421 (M+H)+.

Provenance & Evidence