Potassium Carbonate → HCID 66815652, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 6-(3′-hydroxyphenyl)-pyridine-2-carboxylate (7) (250 mg, 1.1 mmol, 1.0 eq.) and 2-(6′-bromohexyloxy)tetrahydropyran (420 mg, 0.36 mL, 1.6 mmol, 1.5 eq.) in DMF (3 mL) was added K2CO3 (460 mg, 3.3 mmol, 3.0 eq.). The mixture was stirred vigorously overnight at 70° C. and then concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with NaH2PO4 buffer (pH 5, 1M) and brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography on silica using ethyl acetate:hexanes to provide 300 mg (65%) of 12. TLC Rf=0.5 (ethyl acetate:hexanes 1:1), MS m/z 330 (fragment after elimination of the THP group) [M+H]+

Provenance & Evidence