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

Beteiligte Stoffe

Reaktionsschritte

5-chloropyridin-2-amine (100 mg, 778 μmol, Eq: 1.00), 3-chlorobenzaldehyde (115 mg, 93.0 μl, 817 μmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (44.4 mg, 233 μmol, Eq: 0.3) were dissolved in MeOH (1.00 mL) and the intensive yellow solution was stirred for 10 min. To this yellow solution was added dropwise isocyanocyclopropane (52.2 mg, 47.4 μL, 778 μmol, Eq: 1.00) and the corresponding yellow solution was stirred for 2 h. The solvent was removed and the dark red oil was purified twice by flash column chromatography (ethyl acetate in hexanes) to give the product as yellow solid (45 mg, 18.2%). LC/MS (acid polar): 318.1 [M+H]+; 1H-NMR (CDCl3): δ 8.50 (s, 1H), 8.21 (s, 1H), 8.14 (d, 1H), 7.58 (d, 1H), 7.49 (t, 1H), 7.38 (d, 1H), 7.28 (d, 1H), 5.44 (s, 1H), 2.70 (m, 1H), 0.46-0.39 (m, 4H).

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