5-bromo-2,4-difluorobenzoyl chloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl 7-fluoro-1-(4-fluorophenyl)-6-(methyl(pyridin-3-ylmethyl)amino)-4-oxo-1,4-dihydroquinoline-3-carboxylate (U) was prepared from 5-bromo-2,4-difluorobenzoyl chloride via a method analogous to that described in Examples 1 and 9. Compound U (27 mg, 0.060 mmol, 1.0 eq) was dissolved in 1,4-dioxane (0.5 mL) and 1N sodium hydroxide (0.12 mL, 0.12 mmol, 2.0 eq) was added. The reaction was stirred until complete by LCMS, at which time it was neutralized to pH 4-5 with 1N HCl and concentrated to dryness. The residue was suspended in 10% methanol in DCM and filtered. The organics were concentrated to afford 25 mg (99%) of the title compound as an off-white solid that was used without further purification. ES-MS [M+1]+: 422.2. concentrated to dryness filtered The organics were concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl 7-fluoro-1-(4-fluorophenyl)-6-(methyl(pyridin-3-ylmethyl)amino)-4-oxo-1,4-dihydroquinoline-3-carboxylate (U) was prepared from 5-bromo-2,4-difluorobenzoyl chloride via a method analogous to that described in Examples 1 and 9. Compound U (27 mg, 0.060 mmol, 1.0 eq) was dissolved in 1,4-dioxane (0.5 mL) and 1N sodium hydroxide (0.12 mL, 0.12 mmol, 2.0 eq) was added. The reaction was stirred until complete by LCMS, at which time it was neutralized to pH 4-5 with 1N HCl and concentrated to dryness. The residue was suspended in 10% methanol in DCM and filtered. The organics were concentrated to afford 25 mg (99%) of the title compound as an off-white solid that was used without further purification. ES-MS [M+1]+: 422.2. concentrated to dryness filtered The organics were concentrated