Lithium Hydroxide → HCID 59619627, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 8-bromo-1-(1-isopropyl-3-methyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate G, 0.098 mmol), crude acetic acid 2-diacetylamino-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-ylmethyl ester (stage 169.1.1, 0.92 mg) and PdCl2(PPh3)2 (0.0057 mmol) in DMF (1.2 ml) and 1 M aqueous K2CO3 (0.245 ml) was stirred under argon at 105° C. for 1 h. Then the RM was cooled to it and 2 M aqueous LiOH (0.245 ml) was added. The RM was stirred for 1 h 15 min at rt then quenched with 2 M aqueous HCl (0.245 ml), diluted with MeOH and purified directly by Prep.HPLC. The fractions containing product were collected together, basified with NaHCO3, concentrated and extracted with dichloromethane (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered, evaporated and dried under vacuum to give the title compound as a white solid. (HPLC: tR 2.04 min (Method A); M+H=444 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.91 (s, 1H), 8.20 (s, 1H), 8.06-8.02 (m, 1H), 7.97-7.94 (m, 1H), 7.83-7.78 (m, 1H), 7.57-7.54 (m, 1H), 7.45-7.42 (m, 1H), 5.95 (s, br, 2H), 5.20 (t, 1H), 4.55 (hp, 1H), 4.37 (d, 2H), 3.57 (s, 3H), 1.95 (s, 3H), 1.47 (d, 6H))

Provenance & Evidence