Sodium borohydride → HCID 117667676, compound

Participants

Reaction Steps

To the N-(6-bromo-4-oxo-3,4-dihydro-2H-[1,8]naphthyridine-1-carbonyl)-benzamide (188 mg, 0.50 mmol) in 2 mL of MeOH is added NaBH4 (38.0 mg, 1.00 mmol) in one portion. The mixture is stirred for 30 min. and concentrated to dryness. The residue is dissolved in 40 mL EtOAc/H2O, diluted with 10 mL EtOAc and quenched with 20 mL of saturated aqueous NH4Cl. The organic phase is washed with 2×20 mL of H2O and 1×20 mL of brine, dried with MgSO4, filtered and concentrated. The crude material is applied to a silica preparative TLC plate and eluted with 100% EtOAc to give 81.5 mg of 6-bromo-4-hydroxy-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide. This is converted to the titled product using the procedure of Step 5 of Example 22.

Provenance & Evidence