HCID 21956178, compound → 6-Chloro-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

A solution of 2.36 g (7.26 mmol) of the mixture of 3,3-dibromo-6-chloro-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one and 3,3,5-tribromo-6-chloro-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one in THF (70 mL) and saturated ammonium chloride solution (70 mL) was treated with 6 g (92 mmol) of powdered zinc. The mixture was stirred for 2 h, and another 6 g (92 mmol) portion of zinc was added. Stirring was continued another 2 h. The zinc was filtered off and washed with ether. The ether phase was separated, and the aqueous phase was extracted twice with a 1:1 mixture of THF/ether. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated. The crude residue was loaded onto 7.5 g of silica gel and chromatographed on silica gel, eluting with a 90% hexane/10% ethyl acetate to 66% hexane/33% ethyl acetate gradient to give 0.647 g of the title compound. 1H NMR (DMSO-d6): δ 3.57 (s, 2H), 7.04 (d, J=7.6 Hz, 1H), 7.61 (d, J=7.6 Hz, 1H), 11.2 (bs, 1H).

1. stirringStirring
2. waitwas continued another 2 h
3. filtrationThe zinc was filtered off
4. washwashed with ether
5. customThe ether phase was separated
6. extractionthe aqueous phase was extracted twice with a 1:1 mixture of THF/ether
7. dry with materialThe combined organic extracts were dried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customchromatographed on silica gel
11. washeluting with a 90% hexane/10% ethyl acetate to 66% hexane/33% ethyl acetate gradient

ORD record

ord-2d00d07bf73240f287a10a8ba4509dea

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06624171B1