Ammonia → HCID 11718205, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-{[(6-bromopyridin-2-ylmethyl)methylamino]methyl}piperidine-1-carboxylic acid tert-butyl ester (Preparation 4, 88 mg, 0.28 mmol) in toluene (5 mL, anhydrous) was added palladium tetrakis(triphenylphosphine) (13 mg, 0.01 mmol) and sodium carbonate (53 mg in 1.5 mL water, deoxygenated). To the vigorously stirred biphasic mixture was added 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine 57 mg, 0.28 mmol) and the reaction mixture heated to 86° C. (bath) for 3 days. The reaction mixture was allowed to cool to rt then aqueous ammonia (2M, 15 mL) was added with vigorous stirring. After 10 min, ethyl acetate (30 mL) was added and the layers separated. The aqueous was extracted with ethyl acetate (2×20 mL) and the combined organics washed with brine (20 mL), dried (MgSO4), filtered and concentrated in vacuo. Purification via flash chromatography (5% MeOH/CH2Cl2) afforded the title compound: δH (CDCl3): 0.96-1.12 (2H, m), 1.43 (9H, s), 1.63-1.73 (1H, m), 1.78 (2H, d), 2.26-2.32 (5H, m), 2.69 (2H, t), 3.72 (2H, s), 4.00-4.14 (2H, m), 7.51 (1H, d), 7.65 (1H, d), 7.77 (1H, t), 7.88 (2H, d), 8.69 (2H, d). RT=2.38 min; m/z (ES+)=397 [M+H]+.

Provenance & Evidence