Dichloromethane → ethyl [(1S)-5-(3-{[6-(4-methoxyphenyl)-3-(trifluoromethyl)-2-pyridinyl]amino}propoxy)-2,3-dihydro-1H-inden-1-yl]acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl [(1S)-5-(3-{[6-chloro-3-(trifluoromethyl)-2-pyridinyl]amino}propoxy)-2,3-dihydro-1H-inden-1-yl]acetate (Example 306) (0.08 g, 0.18 mmol) in a mixture of toluene (3.75 mL), 1,4-dioxane (0.75 mL), and water (0.88 mL) were added sodium carbonate (0.15 g, 1.38 mmol), 4-methoxyphenyl boronic acid (0.11 g, 0.70 mmol), and PdCl2(dppf).CH2Cl2 (0.03 g, 0.04 mmol). The mixture was stirred at 80° C. for 4 h, and then concentrated under reduced pressure. The product (0.065 g, 70%) was isolated after by silica gel flash chromatography (2:1 hexanes/EtOAc). 1H NMR (400 MHz, CD3OD) δ 1H NMR (400 MHz, CD2Cl2) δ 8.03 (d, 2H), 7.68 (d, 1H), 7.05 (dd, 2H), 6.97 (d, 2H), 6.77 (s, 1H), 6.71 (dd, 1H), 5.39 (b, 1H), 4.15 (q, 2H), 4.09 (t, 2H), 3.90-3.80 (m, 5H), 3.51 (qt, 1H), 2.95-2.78 (m, 2H), 2.71 (dd, 1H), 2.45-2.33 (m, 2H), 2.22-2.10 (m, 2H), 1.80-1.70 (m, 1H), 1.28 (t, 3H).

Provenance & Evidence