Lithium Hydroxide → HCID 58958596, compound

Participants

Reaction Conditions

Reaction Steps

To a solution 2-(4-bromo-5-tert-butyl-2-methyl-2H-pyrazol-3-ylamino)-5-methoxybenzoic acid methyl ester (Example 96, 100 mg, 0.25 mmol), 4-methoxyphenylboronic acid (153.4 mg, 1.01 mmol), PdCl2(dppf).CH2Cl2 (18.46 mg, 0.03 mmol) in a mixture of toluene (6.1 mL) and dioxane (1.22 mL) was added a 2M aqueous solution of sodium carbonate (1.22 mL, 2.44 mmol). A flow of Ar was passed through the reaction mixture for 15 min, and then the reaction was stirred at 75° C. for 18 h. The reaction mixture was then cooled to rt, and filtered through a plug of silica gel. The filtrate was concentrated under reduced pressure, and then the residue was dissolved in a mixture of THF (4 mL), MeOH (2 mL) and water (4 mL). Lithium hydroxide (60 mg, 2.52 mmol) was added, and the mixture was stirred at rt for 18 h. The reaction mixture was then concentrated and the residue purified by preparative HPLC to give the title compound (27.9 mg, 27%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.21 (s, 9H), 3.61 (s, 3H), 3.74 (s, 6H), 6.41 (d, 1H), 6.70 (d, 2H), 7.04 (dd, 1H), 7.09 (d, 2H), 7.39 (d, 1H). ES-MS m/z 410.2 (MH+); HPLC RT (min) 3.66.

Provenance & Evidence