Dichloromethane → HCID 58443272, compound

Participants

Reaction Steps

5-((tert-Butyldimethylsilyloxy)methyl)-2-fluoro-3-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)pyridine (0.204 g, 0.490 mmol) was placed into a flask with 5.0 mL of tetra-butylammonium fluoride in THF and stirred for 4 h. The reaction was then quenched by adding water (5 mL) and extracting with EtOAc (3×5 mL). The combined organic layers were then washed with brine (1×5 mL), dried (MgSO4), filtered, and concentrated. The resulting crude oil (0.145 g, 0.480 mmol) was then placed into a flame-dried flask, and to the reaction mixture was added N-methylmorpholine N-oxide (0.169 g, 1.44 mmol), 4 Å molecular sieves (10 mg), and CH2Cl2 (1.0 mL). Tetrapropylammonium perruthenate (8.43 mg, 0.024 mmol) was then added, and the suspension was stirred at rt overnight. The reaction mixture was worked-up by filtering through Celite® and concentrating the filtrate to give 6-fluoro-5-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)nicotinaldehyde.

Provenance & Evidence