Dimethylformamide → HCID 59860358, compound

Participants

Reaction Conditions

Reaction Steps

Add (2,4-dichlorobenzyl)-[1-(5-iodopyridin-2-yl)-pyrrolidin-3-yl]-amine dihydrochloride (272 mg, 0.61 mmol), triethylborane (1 mL, 1 mmol, 1.0 M in hexanes), tetrakis(triphenylphosphine)palladium(0) (25 mg, 0.031 mmol), and potassium carbonate (253 mg, 1.83 mmol) to anhydrous N,N-dimethylformamide (10 mL). Heat at 65° C. overnight. Dilute with water and extract twice with ethyl acetate. Wash the organic layer with saturated aqueous sodium chloride, dry (magnesium sulfate), filter, concentrate to give a residue. Chromatograph the residue on silica gel eluting with 10:90 to 1:1 ethyl acetate:hexanes, to give the title compound. Combine the title compound and ethyl acetate, add 1 N hydrochloric acid in methanol (1 mL), and concentrate to give the title compound as the hydrochloride salt (35 mg, 13%). 1H NMR (400 MHz, MeOH-d4) δ 7.98 (d, 1H, J=8.8 Hz), 7.80 (s, 1H), 7.69-7.67 (m, 2H), 7.49 (dd, 1H, J=8.0, 2.2 Hz), 7.09 (d, 1H, J=8.8 Hz), 4.50-4.42 (m, 2H), 4.25-4.22 (m, 1H), 4.10-4.05 (m, 1H), 3.90-3.84 (m, 2H), 3.74-3.68 (m, 1H), 2.71-2.61 (m, 1H), 2.64 (q, 2H, J=7.2 Hz), 2.47-2.41 (m, 1H), 1.24 (t, 3H, J=7.2 Hz); MS (ES): m/z=350 [M+H].

Provenance & Evidence