Sodium Carbonate → HCID 67239791, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (preparation described in Intermediate XIX (1), 59 mg, 0.253 mmol), 4-(5-bromo-4-chloro-1,3-thiazol-2-yl)-1,4-diazepan-2-one (75 mg, 0.241 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride (35 mg, 0.048 mmol) in dioxane (0.600 mL) was added 2M aqueous sodium carbonate (0.240 mL, 0.480 mmol). The mixture was heated on a reaction block at 100° C. for 3 hours, and subsequently cooled to room temperature. The dark mixture was filtered through a celite plug, which was rinsed with 10% isopropanol in CHCl3. The eluent was concentrated and purified by preparative HPLC Normal phase, eluting with CH2Cl2/MeOH (0-30%). The 3rd peak was collected and concentrated to give 4-[5-(3-amino-5-methylphenyl)-4-chloro-1,3-thiazol-2-yl]-1,4-diazepan-2-one (45 mg, 0.134 mmol, 29.1% yield) as a brown solid.

Provenance & Evidence