Piconol → HCID 136436899, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of potassium bis(trimethylsilyl)amide (260 mg, 1.32 mmol) and 2-hydroxymethylpyridine (5 ml) was heated at 100° C. for 1 hour, then the title compound of Example 26 (150 mg, 0.26 mmol) added and the reaction mixture stirred at 100° C. for 14 hours. The resulting cool mixture was partitioned between dichloromethane (10 ml) and brine (10 ml), the phases separated and the aqueous phase extracted with dichloromethane (2×10 ml). The combined organic solutions were dried (MgSO4) and evaporated under reduced pressure, then the residual yellow oil purified by column chromatography on silica gel, using dichloromethane: ethyl acetate: methanol (47.5:47.5:5) as eluant, to afford the title compound (35 mg, 21%) as a white solid. δ (CDCl3): 0.94 (3H,t), 1.03 (3H,t), 1.73 (2H,m), 2.40 (2H,q), 2.55 (4H,m), 2.98 (2H,t), 3.14 (4H,m), 5.69 (2H,s), 5.92 (2H,s), 7.07 (1H,d), 7.21 (1H,m), 7.33 (2H,m), 7.62 (1H,m), 7.76 (1H,m), 8.58 (2H,m), 8.81 (1H,s), 8.85 (1H,d), 12.80 (1H,s). LRMS: m/z 630 (M+1)+.

Provenance & Evidence