Lithium Hydroxide → HCID 25116529, compound

Participants

Reaction Steps

The title compound was synthesized as described for Intermediate example I-81 in 53% yield starting from methyl 5-chloropyrazine-2-carboxylate and 3,3,3-trifluoropropan-1-ol. 1 additional equivalent of 3,3,3-trifluoropropan-1-o deprotonated with potassium tert-butoxide was added at 0° C. after stirring 1 h at ambient temperature. Water must have been present because hydrolysis of the ester was performed without adding lithium hydroxide and water. The product was collected by extraction of the acidic water layer with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated in vacuo to give the title compound in a 74:26 mixture with 5-methoxypyrazine-2-carboxylic acid which was also formed in the reaction; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.81 (s, 1 H), 8.30-8.47 (m, 1 H), 4.62 (t, 2 H), 2.78-2.95 (m, 2 H); MS (ESI) m/z 237[M+H+], m/z 235[M−H];

Provenance & Evidence