3-Chlorobenzaldehyde → HCID 74763784, compound

Participants

Reaction Steps

3-bromo-5-chloropyridin-2-amine (200 mg, 964 μmol, Eq: 1.00), 3-chlorobenzaldehyde (142 mg, 115 μl, 1.01 mmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (55.0 mg, 289 μmol, Eq: 0.3) were dissolved in MeOH (1.5 mL) and the intensive yellow solution was stirred for 5 min. To this yellow solution was added dropwise 2-isocyano-2-methylpropane (80.1 mg, 110 μL, 964 μmol, Eq: 1.00) and the corresponding yellow solution was stirred for 3 h. The solvent was removed and the oily residue was treated with dichloromethane and filtered over a cartridge. Two fractions were taken. From fraction 1 the product crystallized after treatment with DMSO-d6. The crystals were filtered off, washed with water and dried under high vacuum to yield the product (48 mg, 12.1%). LC/MS (acid polar): 413.0 [M]+; 1H-NMR (CDCl3): δ 8.62 (s, 1H), 8.26 (s, 1H), 8.17 (d, 1H), 7.65 (s, 1H), 7.43 (t, 1H), 7.34 (d, 1H), 4.91 (s, 1H), 1.03 (s, 9H).

Provenance & Evidence