Chlorotrimethylsilane → HCID 58808722, compound

Participants

Reaction Conditions

Reaction Steps

5′-Ethyl-6′-methoxy-2′-methyl-[2,3′]bipyridinyl-6-carboxylic acid ethyl ester (750 mg, 2.5 mmol) is suspended in acetonitrile and, after addition of KI (1.04 g, 6.25 mmol) and trimethylsilyl chloride, heated to 80° C. under argon for 3 h. This is followed by cooling to room temperature, concentration, addition of 50 ml of water and filtration with suction. The resulting ester (710 mg) is dissolved in MeOH/THF (4/1, 10 ml) and stirred with 1N LiOH solution (7.5 ml) at RT. After 1.5 h, 2N KHSO4 solution is used to acidify, and the precipitate is filtered off with suction. The mother liquor is concentrated and dried in vacuo overnight. The precipitate and the residue are combined and purified by chromatography on silica gel with ethyl acetate/methanol (1/1); yield: 630 mg (98%). MS: m/e=259 (M+H). 1H-NMR (D6-DMSO, δ ppm) 11.65 (s, 1H); 7.91 (t, 1H, J=7.7 Hz); 7.84 (d, 1H, J=7.7 Hz); 7.60 (d, 1H, J=7.7 Hz); 7.51 (s, 1H); 2.42 (q, 2H, J=7.4 Hz); 2.33 (s, 3H); 1.11 (t, 3H, J=7.4 Hz).

Provenance & Evidence