Phosphorus oxychloride → HCID 178518698, compound

Participants

Reaction Steps

To a solution of 4-iodo-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid (4-amino-pyridin-3-yl)-amide (281 mg, 0.79 mmol) in 9 mL pyridine at 0 C was added (slowly) 0.5 mL POCl3 (5.3 mmol). The mixture was stirred at 0 C for 2 hours, then poured on a mixture of ice and saturated aqueous sodium bicarbonate solution. The product precipitates as a colloid. All attempts to filter or extract the product failed. The mixture was concentrated in vacuum, water removed by aceotropic destillation with n-propanol and the crude mixture used as it is. LCMS [M+H]+339, T=0.54 min product and [M+H]+357, T=0.29 min unreacted starting material [YMC ODS-A C18 S7 3.0×50 mm column; 0–100% gradient over 2 min*; 5 mL/min flow rate].* Gradient begins with 10% methanol/90% water (0.1% TFA) and end with 90% methanol/10% water (0.1% TFA)

Provenance & Evidence