2-(2-chloroethyl)-1-methylpiperidine;hydrochloride

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared from pyrazole-4-boronic acid pinacol ester and 2-(2-chloroethyl)-1-methylpiperidine hydrochloride according to Method AC (heating to 90° C. for 6 days before addition of further 2-(2-chloroethyl)-1-methylpiperidine hydrochloride and triethylamine, then heating to 90° C. for a further 3 days) and was isolated as a brown oil (quantitative). LCMS (ES+) 320 (M+H)+, RT 1.85 minutes (Method 1). was isolated as a brown oil (quantitative) LCMS (ES+) 320 (M+H)+, RT 1.85 minutes (Method 1)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-6-nitro-1H-quinolin-2-one (100 mg) and sodium bicarbonate (54 mg) was suspended in 2 mL dry N,N-dimethylformamide and heated to 80° C. on an oil bath. After 30 minutes, sodium iodide (48 mg) was added followed by 2-(2-chloroethyl)-1-methylpiperidine hydrochloride (64 mg) and the mixture stirred at 80° C. for 7 hours. At this time the reaction was cooled to room temperature and quenched by the addition of 25 mL ice/water. The mixture was filtered and the residue washed (1×) with ice water then dried at 40° C. Purification of the crude product by flash chromatography on silica gel (chloroform:10% ammonium hydroxide in methanol, 95:5) gave the title compound (67 mg). At this time the reaction was cooled to room temperature quenched by the addition of 25 mL ice/water The mixture was filtered the residue washed (1×) with ice water then dried at 40° C Purification of the crude product by flash chromatography on silica gel (chloroform:10% ammonium hydroxide in methanol, 95:5)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared from pyrazole-4-boronic acid pinacol ester and 2-(2-chloroethyl)-1-methylpiperidine hydrochloride according to Method AC (heating to 90° C. for 6 days before addition of further 2-(2-chloroethyl)-1-methylpiperidine hydrochloride and triethylamine, then heating to 90° C. for a further 3 days) and was isolated as a brown oil (quantitative). LCMS (ES+) 320 (M+H)+, RT 1.85 minutes (Method 1). was isolated as a brown oil (quantitative) LCMS (ES+) 320 (M+H)+, RT 1.85 minutes (Method 1)