tert-Butyl 4-chloropicolinate → HCID 178450754, compound

Participants

Reaction Steps

To a solution of cis-1-(4-chloro-3-trifluoromethyl-phenyl)-3-(4-hydroxy-cyclohexyl)-urea (0.38 g, 1.13 mmol) and tert-butyl 4-chloropicolinate (0.24 g, 1.13 mmol) in THF (12 mL) was added 1.0 M potassium tert-butoxide solution in THF (3.4 mL, 3.4 mmol) at 0° C. The reaction mixture was allowed to slowly warm to room temperature and then stirred overnight. The reaction was quenched by adding water and the resulting white precipitates were collected and washed with water. Purification by column chromatography (6:4 Hexanes-EtOAc) gave the title compound, 0.32 g (55%) as a yellowish powder. 1H NMR (300 MHz, DMSO-d δ 8.78 (s, 1H), 8.48 (d, J=6 Hz, 1H), 8.09-8.06 (m, 1H), 7.55-7.50 (m, 2H), 7.46 (d, J=2 Hz, 1H), 7.21 (dd, J=6 and 2 Hz, 1H), 6.48 (d, J=8 Hz, 1H), 4.82-4.67 (m, 1H), 3.75-3.59 (m, 1H), 1.91-1.47 (m, 17H).

Provenance & Evidence