3-Chlorobenzaldehyde → [2-(3-Chloro-phenyl)-6-trifluoromethyl-imidazo[1,2-a]pyridin-3-yl]-ethyl-amine

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Reaction Steps

5-(trifluoromethyl)pyridin-2-amine (100 mg, 617 μmol, Eq: 1.00), 3-chlorobenzaldehyde (91.0 mg, 73.7 μl, 648 μmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (35.2 mg, 185 μmol, Eq: 0.3) were dissolved in MeOH (2.00 mL). The resulting colorless solution was stirred at rt. To this solution was added dropwise isocyanoethane (34.0 mg, 45.9 μl, 617 μmol, Eq: 1.00) and the corresponding yellow solution was stirred for 2 h. To the yellow clear solution was added dropwise water until the mixture got turbid and the product precipitated from the MeOH/water mixture. The solid was filtered off, washed with MeOH/water (1:1) and hexane and dried under vacuum, to give a yellow solid (111 mg, 53.0%). MS: 339.0 [M]+; 1H-NMR (D6-DMSO): δ 8.90 (s, 1H), 8.23 (s, 1H), 8.15 (d, 1H), 7.71 (d, 1H), 7.52 (t, 1H), 7.47-7.36 (m, 2H), 5.17 (t, 1H), 3.02 (m, 2H), 1.12 (t, 3H).

Provenance & Evidence