Reaction #163244

Reaction equation

(6-bromopyridin-3-yl)-(1-methyl-1H-pyrazol-3-yl)-amine

{4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester

potassium carbonate

→

title compound

(4-{4-[5-(1-Methyl-1H-pyrazol-3-ylamino)-pyridin-2-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester

Solvents

DME

Conditions

Workup

1. 1
   OtherRemoval of volatiles in vacuo

Procedure

To a solution of (6-bromopyridin-3-yl)-(1-methyl-1H-pyrazol-3-yl)-amine (0.15 g, 0.6 mmol, 1.0 equiv) and {4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester (0.23 g, 0.7 mmol, 1.1 equiv) in 5 Ml DME was added 0.5 Ml saturated potassium carbonate solution followed by 5 mg Pd(PPh3)4 catalyst. The reaction was then heated to 80° C. for 2 h. Removal of volatiles in vacuo followed by silica gel chromatography (20% EtOAc in hexanes) afforded the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.14-1.26 (m, 2H) 1.54 (qd, J=12.59, 2.40 Hz, 2H) 1.68 (br. S., 1H) 1.87 (d, J=11.12 Hz, 5H) 2.31 (d, J=6.57 Hz, 2H) 3.66 (s, 3H) 3.82 (s, 3H) 5.86 (s, 1H) 7.33 (d, J=8.34 Hz, 2H) 7.59 (d, J=2.02 Hz, 1H) 7.80 (d, J=8.84 Hz, 1H) 7.93 (d, J=8.34 Hz, 2H) 7.97 (dd, J=8.84, 2.78 Hz, 1H) 8.65 (d, J=2.27 Hz, 1H) 8.83 (s, 1H); (M+H)+405.2.

Source