Dimethylformamide → HCID 68553177, compound

A mixture of 3-methyl-1H-pyrrolo[2,3-c]pyridine (1.21 g, 9.16 mmol), KOtBu (2.05 g, 18.3 mmol) in DMF (41 mL) is purged with N2 and stirred at rt for 2 h. Chloramine in ether (0.15 M, 92 mL) is added and the mixture is stirred for 20 min. The reaction is cooled to 00 C. and a solution of Na2S2O3 (5 g) in water (80 mL) is added. The mixture is stirred for 10 min, and then concentrated in vacuo. The residue is triturated in DCM and filtered. DCM is added, cooled to 0° C. and charged with BOC2O (541 mg, 2.48 mmol). The resulting mixture is separated by silica gel chromatography eluting with 10% MeOH in DCM to afford 3-methyl-pyrrolo[2,3-c]pyridin-1-yl amine (468 mg, 35%). MS: 148 (M+H); 1H NMR (300 MHz, CDCl3): δ 8.85 (s, 1H), 8.27 (d, 1H), 7.46 (d, 1H), 7.09 (s, 1H), 2.30 (s, 3H).

1. customis purged with N2
2. additionChloramine in ether (0.15 M, 92 mL) is added
3. stirringthe mixture is stirred for 20 min
4. temperatureThe reaction is cooled to 00 C
5. additionand a solution of Na2S2O3 (5 g) in water (80 mL) is added
6. stirringThe mixture is stirred for 10 min
7. concentrationconcentrated in vacuo
8. customThe residue is triturated in DCM
9. filtrationfiltered
10. additionDCM is added
11. temperaturecooled to 0° C.
12. customThe resulting mixture is separated by silica gel chromatography
13. washeluting with 10% MeOH in DCM

ORD record

ord-27f12b68a20c4697b651d13d02a9b3b0

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08258130B2