Tert-Butyl isocyanide → HCID 90159433, compound

Participants

Reaction Steps

5-fluoropyridin-2-amine (200 mg, 1.78 mmol, Eq: 1.00), 3-formylbenzonitrile (246 mg, 1.87 mmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (102 mg, 535 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 (148 mg, 203 μL, 1.78 mmol, Eq: 1.00) and the corresponding yellow solution was stirred for 1 h whereupon a white precipitate was formed. The precipitate was filtered off, washed with MeOH (4 mL) and dried under vacuum to give the product as an off-white solid (323 mg, 58.7%). MS: 308.0 [M]+; 1H-NMR (CDCl3): δ 8.35 (s, 1H), 8.26 (d, 1H), 8.14 (m, 1H), 7.63 (d, 1H), 7.60-7.52 (m, 2H), 7.13 (ddd, 1H), 3.01 (s, 1H), 1.10 (s, 9H).

Provenance & Evidence