Formaldehyde → ((4-chloro-1H-pyrrolo(2,3-b)pyridin-3-yl)methyl)dimethylamine

4-Chloro-7-azaindole (7.32 g, 48 mmol), paraformaldehyde (1.59 g, 52.8 mmol) and dimethylamine hydrochloride (4.32 g, 52.8 mmol) were suspended in 1-butanol (30 mL) and the mixture heated under reflux for 2 hours. The mixture was cooled to ambient temperature and diluted with diethyl ether (50 mL). The resultant solid was collected by filtration and washed with diethyl ether and left to air-dry. The solid was dissolved in water (100 mL) and the pH of the solution adjusted to 11 by the portion-wise addition of solid potassium carbonate. The aqueous phase was extracted with dichloromethane (3×40 mL). The combined organic phase was dried (MgSO4), filtered and evaporated to afford the title compound as a pale yellow solid (7.12 g, 70%). 1H NMR (300 MHz, CDCl3): 11.19 (s, 1H), 8.15 (d, J=5.2 Hz, 1H), 7.32 (s, 1H), 7.08 (d, J=5.2 Hz, 1H), 3.79 (s, 2H), 2.34 (s, 6H).

1. temperaturethe mixture heated
2. temperatureunder reflux for 2 hours
3. filtrationThe resultant solid was collected by filtration
4. washwashed with diethyl ether
5. waitleft
6. customto air-dry
7. dissolutionThe solid was dissolved in water (100 mL)
8. additionthe pH of the solution adjusted to 11 by the portion-wise addition of solid potassium carbonate
9. extractionThe aqueous phase was extracted with dichloromethane (3×40 mL)
10. dry with materialThe combined organic phase was dried (MgSO4)
11. filtrationfiltered
12. customevaporated

ORD record

ord-ad0394e3391142828b367e4e57f25660

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09440976B2