Nitromethane → HCID 86653260, compound

Temperature

0 °C

A solution of aluminum trichloride (0.266 g, 2.00 mmol) in 1:1 DCM:CH3NO2 (5 mL) was added slowly to a slurry of 2,6-difluoro-3-(propylsulfonamido)-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide (0.100 g, 0.254 mmol) in 1:1 DCM:CH3NO2 (2 mL) at 0° C. The solution was stirred at 0° C. for 40 minutes. A solution of 2-chloroacetyl chloride (0.0307 mL, 0.380 mmol) in DCM (1 mL) was added, and the reaction mixture was allowed to warm to room temperature overnight. Additional 2-chloroacetyl chloride (5 eq.) was added, and the reaction mixture was warmed to 50° C. for 20 hours. The solution was cooled and diluted with saturated aqueous ammonium chloride and extracted with EtOAc (3 X). The organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. They were then purified via column chromatography (5% MeOH/DCM) to afford N-(3-(2-chloroacetyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (59 mg, 50%) as a solid.

1. customat 0° C
2. temperatureto warm to room temperature overnight
3. temperaturethe reaction mixture was warmed to 50° C. for 20 hours
4. temperatureThe solution was cooled
5. extractionextracted with EtOAc (3 X)
6. dry with materialThe organic layers were dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThey were then purified via column chromatography (5% MeOH/DCM)

ORD record

ord-8ba30353c9bd4c4391a00059310848a0

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08338452B2