2-Amino-5-bromopyridine → tert-Butyl {4-[5-(6-amino-pyridin-3-yl)-2-methoxy-benzylamino]-cyclohexyl}-methyl-carbamate

Participants

Reaction Steps

Boronic acid 4 (900 mg, 2.29 mmol) is coupled to 2-amino-5-bromopyridine (475 mg, 2.74 mmol) using Method A. On completion, the cooled reaction mixture is diluted with 1 M HCl (10 mL) and extracted with TBME (3×10 mL). The aqueous phase is then basified to pH 9 by careful addition of solid NaHCO3 and extracted into EtOAc (50 mL) and DCM (3×50 mL). The combined organic phases are dried over Na2SO4 and reduced in vacuo to yield the crude title product.

Provenance & Evidence