Potassium Carbonate → HCID 67026903, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (6-chloro-4-methyl-pyridin-2-yl)-diethyl-amine (5.35 g, 26.9 mmol) in DME (75 mL), 2,4,6-trivinylcyclotriboroxane pyridine complex (6.48 g, 26.9 mmol, prepared according to F. Kerins, D. F. O'Shea J. Org. Chem. 67 (2002) 4968-4971) followed by 2 M aq. K2CO3 solution (25 mL) is added. The solution is degassed and put under argon before Pd(PPh3)4 (560 mg, 0.485 mmol) is added. The mixture is stirred for 15 h at 80° C. Another portion of Pd(PPh3)4 (560 mg, 0.485 mmol) is added, and stirring is continued for 6 h. The mixture is cooled to rt, diluted with diethyl ether and washed with sat. aq. NaHCO3. The org. extract is dried over MgSO4, filtered and concentrated. The remaining yellow oil is purified by prep. HPLC to give diethyl-(4-methyl-6-vinyl-pyridin-2-yl)-amine (1.51 g) as a colourless oil; LC-MS: tR=0.68 min, [M+1]+=191.05. 1H NMR (CDCl3): δ 1.20 (t, J=7.0 Hz, 6H), 2.25 (s, 3H), 3.56 (q, J=7.0 Hz, 4H), 5.32 (dd, J=10.5, 2.3 Hz, 1H), 6.23 (dd, J=17.1, 2.0 Hz, 1H), 6.23 (s, 1H), 6.36 (s, 1H), 6.65 (dd, J=17.3, 10.5 Hz, 1H).

Provenance & Evidence