3-Fluorobenzaldehyde → HCID 74763779, compound

Participants

Reaction Steps

5-Fluoropyridin-2-amine (200 mg, 1.78 mmol, Eq: 1.00), 3-fluorobenzaldehyde (240 mg, 205 μL, 1.87 mmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (102 mg, 535 μmol, Eq: 0.3) were dissolved in MeOH (2.5 mL) and the yellow solution was stirred for 10 min. To this yellow solution was added dropwise methyl 2-isocyanoacetate (182 mg, 167 μL, 1.78 mmol, Eq: 1.00) and the corresponding brown solution was stirred for 90 min. Hexane (2 mL) was added and the solvent was removed to give a beige gummy residue. To this residue, MeOH (2 mL) was added and the precipitate was filtered off, washed with MeOH (4 mL) and dried under vacuum to give the product as an off-white solid (172 mg, 30.4%). MS: 318.2 [M+H]+; 1H-NMR (CDCl3): δ 8.23 (m, 1H), 7.78-7.75 (m, 2H), 7.54 (m, 1H), 7.43 (m, 1H), 7.15-7.00 (m, 2H), 3.84 (d, 2H), 3.77 (s, 3H), 3.73 (m, 1H).

Provenance & Evidence