Benzamide, 3-(6-amino-3-pyridinyl)-N-[2-(dimethylamino)ethyl]- synthesis

Yield:-

Reaction Conditions:

with potassium carbonate;bis-triphenylphosphine-palladium(II) chloride in water;N,N-dimethyl-formamide at 130; for 0.222222 h;Microwave irradiation;

Steps:

E.12

To a degassed suspension of 2-amino-5-bromopyridine (0.172 g; 1mmol), and N-(2- dimethylamino-ethyl)-3-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-benzamide (0.318 g; 1 mmol) in DMF (2 ml_) and water (0.5 mL) was added potassium carbonate (414 mg; 3 mmol) and bis(triphenylphosphine)palladium (II) dichloride (32 mg; 5 μmol). The mixture was heated in a Smith Creator microwave at 130⁰C for 800 seconds. The reaction was diluted with ethyl acetate (15 mL) and washed with water (10 mL), brine (10 mL), and dried over MgSO₄, filtered, and evaporated. The crude product was chromatographed on silica eluted with 5% methanol (containing 0.1% ammonia) in dichloromethane. Appropriate fractions were pooled and evaporated to give the title compound as a cream coloured solid (170 mg). ¹H (400MHz, CDCI₃) 8.36 (1H, s), 7.95 (1 H, s), 7.64 (3H, m), 7.50 (1 H, t), 6.80 (1 H, bs), 6.59 (1H, d), 4.53 (2H, bs), 3.54 (2H, q), 2.53 (2H, t), 2.28 (6H, s). LCMS (method B) R_τ 2.70, Ml 285 (M+H⁺).

References:

WO2008/74997,2008,A1 Location in patent:Page/Page column 99