4-Azaindole → Pyrrolo[3,2-b]pyridin-1-ylamine

A solution of pyrrolo[3,2-b]pyridine (1.64 mmol) and potassium tert-butoxide (3.29 mmol) in DMF (7.3 mL) is stirred at rt under N2 for 2 h. 0.15 M NH2Cl. in ether (16.3 mL) is added drop-wise at rt and the reaction mixture is stirred at rt for 3 h. The reaction mixture is quenched with 5% Na2S2O3 aqueous solution (10 mL), and extracted with ether. The combined organic layer is washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with EtOAc to afford pyrrolo[3,2-b]pyridin-1-ylamine (136 mg, 62%) as a solid. MS: 134 (M+H); 1H NMR (300 MHz, CDCl3): δ 4.89 (br, 2N—H), 6.61 (d, H), 7.16 (m, H), 7.38 (d, H), 7.76 (d, H), 8.47 (d, H).

1. customThe reaction mixture is quenched with 5% Na2S2O3 aqueous solution (10 mL)
2. extractionextracted with ether
3. washThe combined organic layer is washed with brine
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue is purified by silica gel chromatography
8. washeluting with EtOAc

ORD record

ord-f197521691ef40888ecc2293e6b42c0b

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08258130B2