Trifluoroacetic acid → 3-Bromo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine

To a cooled (0° C.) solution of 3-bromo-6-trityl-5,7-dihydropyrrolo[3,4-b]pyridine (1.57 g, 3.66 mmol) in chloroform (15 mL) and methanol (15 mL) was added trifluoroacetic acid (30 mL) over 1 min. On complete addition, the solution was stirred for 5 min then the cold bath removed and stirring continued for 30 min. This solution was concentrated under reduced pressure and the residue taken up in HCl (30 mL, 1M aq.). This mixture was extracted with ether (2×20 mL) then the aqueous phase basified with sodium hydroxide (5M aq.). This mixture was extracted with dichloromethane (3×20 mL). The combined dichloromethane extract was dried over magnesium sulfate and concentrated under reduced pressure to give the title compound as a solid.

1. additionOn complete addition
2. customthe cold bath removed
3. stirringstirring
4. waitcontinued for 30 min
5. concentrationThis solution was concentrated under reduced pressure
6. extractionThis mixture was extracted with ether (2×20 mL)
7. extractionThis mixture was extracted with dichloromethane (3×20 mL)
8. extractionThe combined dichloromethane extract
9. dry with materialwas dried over magnesium sulfate
10. concentrationconcentrated under reduced pressure

ORD record

ord-aa8fd62226e14a29a1ba28e1efd5b5ba

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403850B2