Diethylamine → 3,5-Dibromo-N,N-diethylpyridin-4-amine

Participants

Reaction Steps

A mixture of trihalopyridine VII (W=Br) (18.8 g, 70.0 mmol), Et2NH (21.7 mL, 0.210 mol), and N,N-diethylformamide (35 mL) was kept in a sealed high-pressure tube at 170° C. for 20 h. The reaction mixture was cooled to room temperature, dissolved in EtOAc (300 mL), and washed with 1 M K2CO3 (200 mL) and water (8×200 mL). The organic layer was dried with MgSO4 and evaporated in vacuo to give a brown oil. Purification by flash chromatography (CH2Cl2) gave the title compound, 3,5-dibromo-4-(diethylamino)pyridine (VI, R1=R2=Et, W=Br), (20.3 g, 94%) as a yellow oil: Rf =0.45 (CH2Cl2); 1H NMR (250 MHz, CDCl3) δ1.01 (t, J=7.0 Hz, 6H), 3.26 (q, J=7.0 Hz, 4H), and 8.49 (s, 2H); 13C NMR (63 MHz, CDCl3) δ14.10, 46.05, 122.9, 151.9, and 154.1; IR (CHCl3) νmax 2976, 1553, 1457, 1167 cm−1; MS (EI+) m/z (rel intensity) 308 (15%, M+), 193 (100), and 264 (30); HRMS calcd for C9H12Br2N2 (M+) 305.9367, found 305.9366.

Provenance & Evidence