Cesium fluoride → 4-(6-Amino-5-oxazolo[5,4-b]pyridin-2-yl-3-pyridyl)phenol

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-3-oxazolo[5,4-b]pyridin-2-yl-pyridin-2-amine (1 g, Example 9 starting material), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (0.794 g), bis(triphenylphosphine) palladium(II) chloride (0.121 g) and caesium fluoride (1.56 g) in methanol (17 ml) was heated at 120° C. for 20 min in a microwave oven. The reaction was repeated and the reaction mixtures were combined. The resulting mixture was concentrated, then diluted with water (400 ml) and stirred for 30 min. The resulting solid was filtered, washed with water (4×150 ml), dried, washed with diethyl ether (4×150 ml) and dried overnight to give 4-(6-amino-5-oxazolo[5,4-b]pyridin-2-yl-3-pyridyl)phenol (12.3 g) as a solid. NMR Spectrum: (DMSOd6) 6.88 (d, 2H), 7.50-7.57 (m, 3H), 7.72 (bs, 2H), 8.28 (dd, 1H), 8.37-8.42 (m, 2H), 8.53 (d, 1H), 8.55 (bs, 1H); Mass spectrum: M+H+ 355

Provenance & Evidence