Tert-Butyl isocyanide → HCID 74763780, compound

Participants

Reaction Steps

5-(trifluoromethyl)pyridin-2-amine (200 mg, 1.23 mmol, Eq: 1.00), 3-fluorobenzaldehyde (161 mg, 137 μl, 1.3 mmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (70.4 mg, 370 μmol, Eq: 0.3) were dissolved in MeOH (2.00 mL) and the intensive yellow solution was stirred for 20 min. To this yellow solution was added dropwise 2-isocyano-2-methylpropane (103 mg, 140 μl, 1.23 mmol, Eq: 1.00) and the corresponding light yellow solution was stirred for 90 min. The solvent was removed, the remaining solid was treated with MeOH, the precipitate was filtered off, washed with MeOH (2 mL) and dried under vacuum to give the product as a white solid (42 mg, 9.7%). MS: 352.2 [M+H]+; 1H-NMR (CDCl3): δ 8.53 (s, 1H), 7.67-7.53 (m, 3H), 7.35 (m, 1H), 7.24 (dd, 1H), 6.98 (ddd, 1H), 3.06 (s, 1H), 1.01 (s, 9H).

Provenance & Evidence