3,3-Dimethyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one → HCID 21300213, compound

To a solution of 3,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (prepared according to B. Atkinson et al. WO201192293) (153 mg, 943 μmol, Eq: 1.00) in THF (5 mL) at rt was added lithium aluminum hydride, (2 M in THF, 0.95 mL, 1.9 mmol, Eq: 2.01) and the resulting mixture was stirred at rt for 1 h. Additional lithium aluminum hydride, (2 M in THF, 0.95 mL, 1.9 mmol, Eq: 2.01) was added and stirring was continued at rt for 1 h. The reaction mixture was quenched by adding EtOAc (˜2 mL) followed by water (˜1 mL). To the resulting slurry was added aqueous Rochelle's salt solution (20 mL) and the mixture was extracted with EtOAc (2×20 mL). The crude material was purified by flash chromatography (silica gel, 12 g, 0% to 100% EtOAc in hexanes) to give 3,3-dimethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine (73 mg), m/z=149 (M+H).

1. stirringstirring
2. waitwas continued at rt for 1 h
3. customThe reaction mixture was quenched
4. additionby adding EtOAc (˜2 mL)
5. additionTo the resulting slurry was added aqueous Rochelle's salt solution (20 mL)
6. extractionthe mixture was extracted with EtOAc (2×20 mL)
7. customThe crude material was purified by flash chromatography (silica gel, 12 g, 0% to 100% EtOAc in hexanes)

ORD record

ord-d90dced4003e4d12a6ecf4fae89f7717

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309248B2