Cesium fluoride → Tert-butyl 4-[4-[6-amino-5-(6-fluorooxazolo[4,5-b]pyridin-2-yl)-3-pyridyl]pyrazol-1-yl]piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazol-1-yl]piperidine-1-carboxylate (222 mg) and 5-bromo-3-(6-fluorooxazolo[4,5-b]pyridin-2-yl)pyridin-2-amine (140 mg), bis(triphenylphosphine) palladium (II) chloride (15.9 mg) and caesium fluoride (172 mg) were weighed out in a microwave vial and sealed. Methanol (2 ml) was added and nitrogen was bubbled in the resulting suspension. The resulting mixture was heated in a 300 W microwave at 120° C. for 20 minutes. The crude product was purified by flash chromatography on silica gel (dried deposit with silica gel) eluting with 0 to 5% methanol in dichloromethane. The solvent was evaporated to dryness to afford tert-butyl 4-[4-[6-amino-5-(6-fluorooxazolo[4,5-b]pyridin-2-yl)-3-pyridyl]pyrazol-1-yl]piperidine-1-carboxylate (190 mg). NMR Spectrum: (CDCl3) 1.49 (s, 9H), 1.94-2.03 (m, 2H), 2.16-2.24 (m, 2H), 2.84-3.00 (m, 2H), 3.28 (bs, 2H), 3.29-3.37 (m, 1H), 6.94 (bs, 2H), 7.66 (dd, 1H), 7.68 (s, 1H), 7.79 (s, 1H), 8.35 (d, 1H), 8.45 (d, 1H), 8.48 (dd, 1H); Mass spectrum: M+H+ 480.

Provenance & Evidence