Sodium Carbonate → 4-[5-(3-Amino-5-nitrophenyl)-1,3-thiazol-2-yl]-1,4-diazepan-2-one

Participants

Reaction Conditions

Reaction Steps

4-(5-Bromo-1,3-thiazol-2-yl)-1,4-diazepan-2-one (Step 5 of Intermediate XX, 1.96 g, 7.10 mmol), (3-amino-5-nitrophenyl)boronic acid (1.291 g, 7.10 mmol), tetrakis-(triphenylphosphine)palladium(0) (0.410 g, 0.355 mmol), 1,2-dimethoxyethane (42 mL) and 2M aqueous sodium carbonate (10.65 mL, 21.29 mmol) were successively introduced in a high pressure reaction vessel. The headspace was flushed with nitrogen, the vessel capped and the mixture was stirred at 100° C. for 18 h. The reaction was then cooled to room temperature and 25% aqueous ammonium acetate was added. The aqueous layer was extracted with ethyl acetate (3×). The combined organics were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. Purification via CombiFlash (ethanol/ethyl acetate) afforded 590 mg (1.77 mmol, 25% yield) of 4-[5-(3-amino-5-nitrophenyl)-1,3-thiazol-2-yl]-1,4-diazepan-2-one as a yellow solid. MS APCI: [M+H]+ m/z 334.1.

Provenance & Evidence