Cesium carbonate → 4-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)benzenamine

Participants

Reaction Conditions

Reaction Steps

4-(2-Chloro-pyridin-4-yloxy)-phenylamine (0.7 g, 3.2 mmol), 1-methyl-4-(4,4,5,5-tetramethyl)-[1,3,2]dioxaborolan-2-yl)-4H-pyrazole (1.0 g, 4.8 mmol), Cs2CO3 (4.0 g, 12.3 mmol) and Pd(PPh3)4 (0.45 g, 0.4 mmol) were combined in a mixture of DMF and water (3:1, 20 mL). The reaction mixture was degassed, blanketed with argon and heated to 90° C. overnight. The reaction mixture was diluted with water and extracted with EtOAc (3×50 mL). The combined organics were washed with saturated brine, dried (MgSO4), concentrated in vacuo and purified by silica gel chromatography to provide 4-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)benzenamine (0.7 g, 74% yield). 1H NMR (300 MHz, DMSO-d6), δ 8.29 (d, J=5.7 Hz, 1 H), 8.19 (s, 1 H), 7.90 (s, 1 H), 7.10 (d, J=2.4 Hz, 1 H), 6.83 (d, J=8.7 Hz, 2 H), 6.62 (d, J=8.7 Hz 2 H), 6.52 (dd, J=2.4, 5.7 Hz, 1 H), 5.10 (s, 2 H), 3.84 (s, 3 H); MS (ESI) m/z: 267.3 (M+H+)

Provenance & Evidence