Methylamine → [3-(1-Ethylpropoxy)-6-(2-methoxy-4-trifluoromethoxyphenyl)-5-methylpyridin-2-yl]-methylamine

Participants

Reaction Conditions

Reaction Steps

Pd2dba3 (4 mg) is added to a solution of compound 45 (70 mg, 0.173 mmol) in toluene (1 ml), followed by the addition of P(t-Bu)3 (1.4 mg), methylamine (2M in THF, 0.17 ml, 0.347 mmol) and t-BuOK (1M in THF, 0.26 ml, 0.26 mmol). The resulting mixture is sealed and heated to 55° C. overnight, then cooled to room temperature. The reaction mixture is diluted with 30% EtOAc in hexane, washed with water, brine, dried, filtered and evaporated. The crude product is purified by chromatograph (eluted with 6% EtOAc in hexane) to give the product 48 as a light yellow solid. 1H NMR (CDCl3) δ 0.97 (t, J=7.6 Hz, 6H), 1.71 (m, 4H), 1.98 (s, 3H), 2.99 (s, 3H), 3.79 (s, 3H), 4.13 (m, 1H), 4.77 (brs, 1H), 6.67 (s, 1H), 6.77 (s, 1H), 6.87 (dd, 1H), 7.32 (d, J=8.4 Hz, 1H). LCMS 399.4 (M+1).

Provenance & Evidence