Potassium Carbonate → {2-[4-(4-Cyanopyridin-2-yloxy)phenyl]ethyl}carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

[2-(4-Hydroxyphenyl)-ethyl]-carbamic acid tert-butyl ester (5.31 g, 22.4 mmol) and 2-chloroisonicotinonitrile (3.27 g, 22.4 mmol) were dissolved with magnetic stirring in dimethyl sulfoxide (DMSO; 50 mL) in a 250 mL round bottom flask equipped with a reflux condenser and a dry nitrogen line at 25° C. To the solution was added K2CO3 (6.0 g, 43.5 mmol), and the reaction mixture was slowly heated to 135-140° C. over 1 h. The reaction was filtered, concentrated in vacuo, and diluted with H2O (500 mL). The precipitate which formed was collected by suction filtration, dissolved in CH2Cl2 and treated with decolorizing carbon. The mixture was filtered and concentrated in vacuo to afford {2-[4-(4-cyanopyridin-2-yloxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester (5.57 g) as a beige solid: mp 92-96° C.; 1H-NMR (CDCl3) δ 8.32 (d, J=5.3 Hz, 1H), 7.26 (m, 2H), 7.20 (dd, J=5.1, 0.8 Hz, 1H), 7.16 (m, 1H), 7.10-7.04 (m, 3H), 3.40 (br m, 2H), 2.83 (m, 2H), 1.45 (s, 9H); ESIMS m/z 284.2 ([M−C4H8+H]+). This material was used without further purification in the next step.

Provenance & Evidence