Sodium Carbonate → HCID 10654534, compound

Participants

Reaction Conditions

Reaction Steps

To a pressure tube containing a magnetic stir bar was added N,N-dimethylpropargylamine (333 mg, 4 mmol) and the vial was purged with argon. To the tube is added a solution of tetrakis(triphenylphosphine)palladium(0) (139 mg, 0.12 mmol) in ethanol/dimethoxyethane (1:1, 2 mL), sodium carbonate(aq) (2 M, 4 mL, 4 mmol), copper(I)iodide (46 mg, 0.24 mmol) and the vial was once again purged with argon. The resultant solution was stirred at room temperature for 5 min when 3-bromopyridine (483 μL, 5 mmol) was added as a neat oil. The tube was purged with argon, capped, heated to 90° C. and stirred for 1 h. The solution was cooled to room temperature and poured into a flask containing anhydrous sodium sulfate (5 g). The solution was dried for 10 min, filtered and the solvent was removed in vacuo. The crude material was chromatographed on silica gel (CH3OH/CHCl3, 10/90, Rf=0.13) to afford the title compound 51 (26 mg, 4% yield) as a brown oil: 1H NMR (CDCl3) δ 8.67 (br s, 1H), 8.52 (m, 1H), 7.72 (m, 1H), 7.24 (m, 1H), 3.49 (s, 2H), 2.37 (s, 6H); LRMS (ESI) m/z calcd for C10H12N2 [M+H]+ 161. found 161; LRMS (ESI) m/z calcd for C8H6N [M−N(CH3)2]+ 116. found 116; HRMS (ESI) m/z calcd for C10H12N2 [M+H]+ 161.1079. found 161.1090; HPLC>98% (tR=9.38 min, 60 (A):40 (B): 0.02 (C); tR=4.70 min, 60 (A):40 (B): 0.07 (C)).

Provenance & Evidence