Water → 6-Methyl-5-((6'-methyl-[2,3'-bipyridin]-4-yl)oxy)pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of Example A7 (2.8 g, 11.88 mmol), 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (3.38 g, 15.45 mmol) and K2CO3 (3.28 g, 23.76 mmol) in dioxane 48 mL) and water (12 mL) was sparged with Ar, treated with Pd(PPh3)4 (1.373 g, 1.188 mmol) and heated at 85° C. overnight. The mixture was cooled to RT, diluted with EtOAc, the solids removed via filtration through diatomaceous earth and the filtrate concentrated to dryness and purified via silica gel chromatography (MeOH/DCM). The material was treated with MeCN, the solid collected via filtration and re-purified via silica gel chromatography (MeOH/DCM) to afford 6-methyl-5-((6′-methyl-[2,3′-bipyridin]-4-yl)oxy)pyridin-2-amine (3.08 g, 89%). 1H NMR (400 MHz, DMSO-d6): δ 9.56 (d, J=2.4 Hz, 1 H), 8.96 (d, J=5.7 Hz, 1 H), 8.71 (dd, J=8.1, 2.4 Hz, 1 H), 7.86 (d, J=2.4 Hz, 1 H), 7.76 (d, J=8.1 Hz, 1 H), 7.66 (d, J=8.7 Hz, 1 H), 7.18 (dd, J=5.7, 2.4 Hz, 1 H), 6.94 (dd, J=8.6, 0.7 Hz, 1 H), 5.86 (s, 2 H), 2.97 (s, 3 H), 2.59 (s, 3 H); MS (ESI) m/z: 293.1 (M+H+).

Provenance & Evidence