Tert-Butyl isocyanide → HCID 74220977, compound

Participants

Reaction Steps

5-(trifluoromethyl)pyridin-2-amine (100 mg, 617 μmol, Eq: 1.00), 3-ethynylbenzaldehyde (84.3 mg, 648 μmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (35.2 mg, 185 μmol, Eq: 0.3) were dissolved in MeOH (1.00 mL) and the intensive yellow solution was stirred for 5 min. To this yellow solution was added dropwise 2-isocyano-2-methylpropane (51.3 mg, 70.2 μL, 617 μmol, Eq: 1.00) and the corresponding yellow solution was stirred for 2 h. Water was added, the oil was separated from water/MeOH phase and purified by flash column chromatography (40 g SiO2, Hex/EtOAc 100:0 to 0:100) to yield a yellow solid (120 mg, 54.4%). MS: 357.0 [M]+; 1H-NMR (D6-DMSO): δ 8.89 (s, 1H), 8.38 (s, 1H), 8.27 (d, 1H), 7.72 (d, 1H), 7.52-7.40 (m, 3H), 4.94 (s, 1H), 4.22 (s, 1H), 1.04 (s, 9H).

Provenance & Evidence