1,2-Dimethoxyethane → 2-Methylpentane

Participants

Reaction Steps

Dissolve a mixture of (S)-[1-(5-bromopyridin-2-yl)-pyrrolidin-3-yl]-(2,4-dichlorobenzyl)-amine (330 mg, 0.82 mmol), phenylboronic acid (100 mg, 0.82 mmol), tetakis(triphenylphosphine)palladium (0) (50 mg, 0.04 mmol), 2 N sodium carbonate solution (0.5 mL, 3.3 mmol) in 15:85 ethylene glycol dimethyl ether:methanol (8 mL) and heat in microwave (CEM Discover, 200W) at 80° C. for 20 min. Concentrate to a residue and dissolve in chloroform and wash with saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate, and chromatograph on silica gel, eluting with 0:100 to 10:90 methanol:chloroform, then second column eluting with 0:100 to 50:50 ethyl acetate:2-methylpentane) to give the title compound as a residue. Treatment of the residue essentially as described in Example 1 gives the title compound as its hydrochloride. 1H NMR (400 MHz, DMSO-d6) δ 8.32 (1H, d, J=1.96 Hz), 8.12 (1H, dd, J=9.05, 2.20 Hz), 7.71-7.77 (2H, m), 7.64 (2H, d, J=7.58 Hz), 7.54 (1H, dd, J=8.31, 2.20 Hz), 7.47 (2H, t, J=7.58 Hz), 7.37 (1H, d, J=7.34 Hz), 6.93 (1H, d, J=9.05 Hz), 4.36 (2H, d, J=4.65 Hz), 4.09-4.16 (1H, m), 3.91-4.00 (2H, m), 3.82-3.89 (1H, m), 3.71-3.80 (1H, m), 2.50-2.56 (1H, m), 2.37-2.45 (1H, m), MS (ES): m/z=398 [M+].

Provenance & Evidence