Water → 1H,2H,3H-pyrrolo[3,2-b]pyridine

To a solution of 1H-pyrrolo[3,2-b]pyridine (1.18 g, 10 mmol) in 100 mL of THF, was added borane tetrahydrofuran complex (60 mL of a 1 M solution, 6 eq) and the mixture was heated at reflux for 5 h. After allowing the reaction to cool down to room temperature, water was added slowly and the solution was extracted with ethyl acetate twice. The combined extracts were washed with a saturated solution of sodium bicarbonate, dried over sodium sulfate and evaporated. The residue was purified on silica gel (eluent: 15% methanol in DCM) to give 0.17 g of 2,3-dihydro-1H-pyrrolo[3,2-b]pyridine 1-1.

1. temperaturewas heated
2. temperatureat reflux for 5 h
3. customthe reaction
4. extractionthe solution was extracted with ethyl acetate twice
5. washThe combined extracts were washed with a saturated solution of sodium bicarbonate
6. dry with materialdried over sodium sulfate
7. customevaporated
8. customThe residue was purified on silica gel (eluent: 15% methanol in DCM)

ORD record

ord-73c7668e79eb4aa489b4fd10d619cb39

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481731B2