Ammonium Chloride → HCID 67070070, compound

Participants

Reaction Conditions

Reaction Steps

step 2—To a suspension of 316 (595 mg, 1.12 mmol) in a 1:1 mixture of MeOH/H2O (4 mL each) at RT was added NH4Cl (601 mg, 11.2 mmol) and iron powder (314 mg, 5.62 mmol). The reaction mixture was warmed to 105° C. and stirred overnight. The reaction was cooled to RT and filtered via Büchner funnel and the filtrate was rinsed with DCM. The filtrate was diluted with H2O and extracted with DCM. The extracts were washed with H2O and brine. The combined aqueous phases were back-extracted with DCM. The combined organic extracts were combined, dried (MgSO4), filtered, and concentrated. The crude residue was purified by SiO2 chromatography, eluting with an EtOAc/hexane gradient (0% to 40% EtOAc) to afford 405 mg (72%) of 4-amino-N-[5-(2-benzyloxy-pyridin-3-yl)-3-tert-butyl-2-methoxy-phenyl]-3-fluoro-benzamide (318) as a foamy, yellow solid.

Provenance & Evidence