Cesium carbonate → HCID 86719344, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (6-bromo-5-(2-((tert-butyldimethylsilyl)oxy)ethoxy)pyridin-2-yl)methanol (2.18 g, 6.0 mmol), 1-isopropylpiperazine (0.92 g, 7.2 mmol), BINAP (0.37 g, 0.6 mmol), and Cs2CO3 (3.18 g, 9.0 mmol) in nitrogen saturated toluene (40 mL) was added palladium(II) acetate (0.13 g, 0.6 mmol). The resulting mixture was heated at 100° C. for 18 h. After that time the reaction was cooled to rt, diluted with brine and extracted with ethyl acetate. The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The product was purified by flash column chromatography (silica gel, 95:5 dichloromethane/methanol to 90:10 dichloromethane/methanol) to give (5-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-6-(4-isopropylpiperazin-1-yl)pyridin-2-yl)methanol (1.07 g, 44%) as a sticky yellow solid: 1H NMR (400 MHz, CDCl3): δ 7.05 (d, J=7.6 Hz, 1H), 6.66 (d, J=8.0 Hz, 1H), 4.59 (s, 2H), 4.06-3.97 (m, 4H), 3.53 (br s, 4H), 2.68 (m, 5H), 1.10 (d, J=6.4 Hz, 6H), 0.90 (s, 9H), 0.09 (s, 6H).

Provenance & Evidence