Pyridine → HCID 69028441, compound

Participants

Reaction Conditions

Reaction Steps

To solution of 18 (46 mg, 0.25 mmol) in 1 mL of CH2Cl2 was added dry pyridine (20 mg, 50 μL, 0.3 mmol) at 0° C. (FIG. 2D). The solution was stirred at 0° C. for 10 minutes followed by the addition of acetyl chloride (~30 μL, 0.4 mmol). The reaction mixture was stirred overnight at 0° C. and then the solvent was removed under vacuo. The residue was partioned between water and EtOAc. The organic solution was washed with 1 M HCl (10 mL), water (50 mL), and then dried (MgSO4). The solvent was evaporated to afford a oil which was chromatographed on silica gel and eluted with hexanes:EtOAc (initially 70:30, then 50:50) to afford the desired product as a white solid (11 mg, 20% yield). 1H NMR (CDCl3) δ 7.86-7.89 (d, 1H, ArH), 7.46-7.44 (d, 1H, ArH), 7.32-7.36 (t, 1H, ArH), 2.45 (s, 3H, SCH3), 2.38 (s, 3H, CH3); FAB-MS 227 (MH+, 15) 226 (MH+ -1, 10), 167 (50), 157 (30), 102 (100).

Provenance & Evidence