3-Amino-4-chlorobenzoic acid → HCID 67056869, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-amino-4-chlorobenzoic acid (509 mg) in THF (8 mL) was added dropwise an 1 M THF solution of lithium 1,1,1,3,3,3-hexamethyldisilazan-2-ide (6 mL) while keeping the internal temperature below −5° C. under a nitrogen atmosphere, and the mixture was stirred around −5° C. for 30 min. To the solution was added dropwise a solution of 1-(2,6-difluorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarbonyl chloride (800 mg) in THF (8 ml), and the resulting mixture was stirred around −5° C. for 1 hr. The reaction mixture was partitioned between EtOAc (16 mL) and 1 M HCl (16 mL). The aqueous layer was extracted with EtOAc (8 mL). The organic layers were combined, washed with brine two times, dried over MgSO4, filtered and evaporated in vacuo. The residue was triturated with CH2Cl2, and the precipitates produced were collected by filtration. The isolated product was triturated with MeOH and collected by filtration to give 4-chloro-3-({[1-(2,6-difluorophenyl)-6-oxo-1,6-dihydro-3-pyridinyl]carbonyl}amino)benzoic acid (288 mg).

Provenance & Evidence