1-chloroethyl pentanoate

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of N-(3-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)propane-1-sulfonamide (0.3 g, 0.61 mmol) in anhydrous DMF (2.5 mL) was added KOH (69 mg, 1.23 mmol). The reaction was stirred at 10° C. for 30 min, followed by adding a solution of 1-chloroethyl pentanoate (0.1 g, 0.61 mmol) in anhydrous DMF (0.5 mL) dropwise over 30 min. The mixture was stirred at 10° C. for another 16 h, then diluted with EtOAc (40 mL) and filtered. The filtrate was concentrated in vacuo and the residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=7/1) to give the crude product. The crude product was recrystallized in PE/EtOAc (10/1) to give the title compound as a white solid (0.14 g, 37.8%). The title compound was characterized by LC-MS and 1H NMR as shown below: The mixture was stirred at 10° C. for another 16 h filtered The filtrate was concentrated in vacuo the residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=7/1) to give the crude product The crude product was recrystallized in PE/EtOAc (10/1)

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of N-(3-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)propane-1-sulfonamide (0.3 g, 0.61 mmol) in anhydrous DMF (2.5 mL) was added KOH (69 mg, 1.23 mmol). The reaction was stirred at 10° C. for 30 min, followed by adding a solution of 1-chloroethyl pentanoate (0.1 g, 0.61 mmol) in anhydrous DMF (0.5 mL) dropwise over 30 min. The mixture was stirred at 10° C. for another 16 h, then diluted with EtOAc (40 mL) and filtered. The filtrate was concentrated in vacuo and the residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=7/1) to give the crude product. The crude product was recrystallized in PE/EtOAc (10/1) to give the title compound as a white solid (0.14 g, 37.8%). The title compound was characterized by LC-MS and 1H NMR as shown below: The mixture was stirred at 10° C. for another 16 h filtered The filtrate was concentrated in vacuo the residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=7/1) to give the crude product The crude product was recrystallized in PE/EtOAc (10/1)