Trifluoroacetic acid → HCID 57963161, compound

Participants

Reaction Steps

5-Iodo-6-methyl-pyridin-2-ylamine (63, 1.7 g, 7.3 mmol) and 6-methoxy-pyridine-3-carbaldehyde (64, 1.1 g, 8.0 mmol) were combined in a round bottom flask with trifluoroacetic acid (2.80 mL, 36.3 mmol), triethylsilane (5.80 mL, 36.3 mmol) and 50 mL of acetonitrile. The reaction was stirred at room temperature overnight, then heated to reflux for 6 hours. The reaction was concentrated under vacuum, combined with aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel flash column chromatography, eluting with 10-100% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (65, 1.80 g). MS (ESI)[M+H+]+=356.80.

Provenance & Evidence