Water → 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

To a solution of 5-bromo-7-azaindole (2.0 g, 10.1 mmol) in DCM (50 mL) was added AlCl3 (6.8 g, 51.0 mmol). The suspension was stirred at RT for 10 min and trichloroacetyl chloride (2.8 g, 15.40 mmol) was added slowly. The mixture was stirred at RT for overnight and then poured into iced-water. The aqueous solution was extracted with DCM three times, and organic layers were combined and evaporated. The crude solid was dissolved in THF (50 mL) and treated with water (25 mL) and triethylamine (5 mL) at RT for 6 h. The solvents were then removed by evaporation and the resulting solid was poured into 1N HCl solution. The crude product was collected by filtration and washed with water. After drying on the pump for over night, a white solid was obtained (2.4 g, 9.96 mmol). MS (ES+): m/e=241.0 (M+H); LC: 2.7 min.

1. stirringThe mixture was stirred at RT for overnight
2. extractionThe aqueous solution was extracted with DCM three times, and organic layers
3. customevaporated
4. dissolutionThe crude solid was dissolved in THF (50 mL)
5. additiontreated with water (25 mL) and triethylamine (5 mL) at RT for 6 h
6. customThe solvents were then removed by evaporation
7. additionthe resulting solid was poured into 1N HCl solution
8. filtrationThe crude product was collected by filtration
9. washwashed with water
10. customAfter drying on the pump for over night
11. customa white solid was obtained (2.4 g, 9.96 mmol)
12. custom2.7 min.

ORD record

ord-9a497f93ee804bea8539c1a79c7520f5

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07446199B2