2-Iodoxybenzoic acid → HCID 86719345, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (5-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-6-(4-isopropylpiperazin-1-yl)pyridin-2-yl)methanol (1.07 g, 2.61 mmol) in 1,2-dichloroethane (20 mL) under nitrogen was added 2-iodoxybenzoic acid (0.88 g, 3.14 mmol) at rt. The reaction mixture was stirred at 80° C. for 1.5 h. After that time the reaction was cooled to rt and concentrated under reduced pressure. The product was purified by flash column chromatography (silica gel, 95:5 dichloromethane/methanol) to give 5-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-6-(4-isopropylpiperazin-1-yl)picolinaldehyde (0.63 g, 59%) as a brown solid: 1H NMR (400 MHz, CDCl3): δ 9.85 (s, 1H), 7.59 (d, J=8.4 Hz, 1H), 7.17 (d, J=8.0 Hz, 1H), 4.19-4.15 (m, 2H), 4.02-3.88 (m, 6H), 3.56-3.48 (m, 1H), 3.20 (br s, 4H), 1.37 (d, J=6.4 Hz, 6H), 0.90 (s, 9H), 0.09 (s, 6H); ESI MS m/z 408 [M+H]+.

Provenance & Evidence