Methyl vinyl sulfone → HCID 86671273, compound

Participants

Reaction Conditions

Reaction Steps

Methylsulfonylethene (commercially available from Sigma-Aldrich, St. Louis, Mo.) (142 mg, 1.33 mmol) was added dropwise to a solution of 2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine (150 mg, 0.89 mmol, commercially available from D-L Chiral Chemicals, ST-0143) in EtOH (10 mL). The reaction mixture was stirred at 60° C. for 2 hours, and then concentrated and purified by flash chromatography on silica gel eluting with 0% to 5% MeOH in DCM to give 2-chloro-6-(2-(methylsulfonyl)ethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine (220 mg, 90% yield). 1H NMR (400 MHz, CD3OD) δ ppm 2.91-3.11 (9H, m) 3.43 (2H, t, J=6.65 Hz) 3.73-3.77 (2H, m) 7.26 (1H, d, J=8.22 Hz) 7.56 (1H, d, J=8.02 Hz) ppm; LC/MS m/z: 275 (M+1).

Provenance & Evidence