Tetrahydrofuran → 7-Chloro-4-iodo-1,3-dimethyl-1H-pyrrolo[2,3-c]pyridine

To a solution of 7-chloro-4-iodo-3-methyl-1H-pyrrolo[2,3-c]pyridine (2 g) in dry tetrahydrofuran (100 ml) at 0° C. under argon was added portionwise sodium hydride (60% dispersed in mineral oil 603 mg). After addition the ice-bath was removed and the solution stirred at room temperature for 30 minutes. The solution was re-cooled to 0° C. and a solution of methyl iodide (3.41 ml) in dry tetrahydrofuran (40 ml) was added dropwise. The solution was allowed to warm to room temperature and stirred overnight. The solution was evaporated and the residue partitioned between ethyl acetate (200 ml) and water (100 ml). Washed with water (2×100 ml, pH7) then dried (MgSO4), filtered and evaporated to an orange/yellow solid. The solid was stirred in hexane for 2 h then filtered off and dried to give the title compound (1.19 g).

1. customwas removed
2. temperatureThe solution was re-cooled to 0° C.
3. additiona solution of methyl iodide (3.41 ml) in dry tetrahydrofuran (40 ml) was added dropwise
4. temperatureto warm to room temperature
5. stirringstirred overnight
6. customThe solution was evaporated
7. customthe residue partitioned between ethyl acetate (200 ml) and water (100 ml)
8. washWashed with water (2×100 ml, pH7)
9. dry with materialthen dried (MgSO4)
10. filtrationfiltered
11. customevaporated to an orange/yellow solid
12. stirringThe solid was stirred in hexane for 2 h
13. filtrationthen filtered off
14. customdried

ORD record

ord-d02aa750703a40c899d9dd4e3d84b099

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07589206B2