Dichloromethane → HCID 90414326, compound

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared using similar methods to those in Example 33 using 1-bromo-3-(bromomethyl)benzene in Step A and by inserting the following procedure between Step E and F. To a 5 mL microwave vial were added a stirbar, ethyl 3-(1-(3-bromobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoate (230 mg, 0.4 mmol), 6-methoxypyridin-3-ylboronic acid (92 mg, 0.6 mmol), Pd(dppf)Cl2.CH2Cl2 (29 mg, 0.04 mmol), and K2CO3 (221 mg, 1.6 mmol). The vial was capped and flushed with nitrogen before adding 8 mL of N2 sparged 1,4-dioxane and 2 mL of N2 sparged water. The resulting mixture was heated at 80° C. for 12 hours. The vial was cooled to RT, concentrated to dryness, and subjected to FCC purification to afford ethyl 3-(1-(3-(6-methoxypyridin-3-yl)benzyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoate. MS (ESI): mass calcd. for C37H36N4O4, 600.27; m/z found, 601.1 [M+H]+. The title compound was then prepared using similar methods to those in Example 33 Step F to afford the title compound. MS (ESI): mass calcd. for C35H32N4O4, 572.24; m/z found, 573.3 [M+H]+. 1H NMR (300 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.43-8.32 (m, 2H), 8.02 (d, J=8.5, 1H), 7.97 (d, J=8.3, 1H), 7.90 (dd, J=8.7, 2.5, 1H), 7.81-7.73 (m, 1H), 7.67 (d, J=8.5, 1H), 7.60 (t, J=7.4, 1H), 7.53 (d, J=6.9, 1H), 7.45-7.31 (m, 3H), 7.18 (d, J=1.6, 1H), 6.98-6.85 (m, 3H), 5.52 (s, 2H), 5.36 (s, 2H), 3.87 (s, 3H), 3.07 (s, 2H), 1.25 (s, 6H).

Provenance & Evidence