Sodium Carbonate → HCID 67480116, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl N-[[4-[5-[2-[bis(tert-butoxycarbonyl)amino]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridyl]isoxazol-3-yl]-3-fluoro-phenyl]methyl]-N-methyl-carbamate (322.6 mg, 0.3339 mmol) and 2-bromo-5-isopropylsulfonyl-pyridine (105.8 mg, 0.4007 mmol) in DMF (3 mL) was degassed and placed under an atmosphere of nitrogen. Pd(PPh3)2Cl2 (13.81 mg, 0.03339 mmol) was added and the reaction again degassed. 2M aqueous Na2CO3 (501.0 μL, 1.002 mmol) was added and the reaction was stirred at 95° C. for 2 hours. The reaction mixture was partitioned between EtOAc and brine and the aqueous layer extracted with EtOAc (×3). The combined organic extracts were washed with water (×3) and brine (×2), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion™, 40 g column, loading with DCM and eluting with 0 to 50% EtOAc/Petroleum Ether) to give the impure sub-title compound as a yellow oil which was used in the next step without purification.

Provenance & Evidence