Methyl iodide → 2-Ethyl-1H-pyrrolo(2,3-b)pyridine

To a solution of 2-methyl-7-azaindole (1.32 g, 10 mmol) in dry diethyl ether (60 ml) at room temperature under an inert atmosphere is added n-BuLi (18.8 ml of a 1.6 M solution in hexanes, 30 mmol) followed by t-BuOK (2.24 g, 20 mmol). The reaction mixture is stirred at room temperature for 40 minutes and then cooled to −70° C. whereupon methyl iodide (1.25 ml, 20 mmol) is added dropwise. Stirring continues for a further 2 hours after which time, the reaction mixture is quenched with water (2 ml) and is allowed to slowly warm to room temperature. The cooled solution is poured onto water (200 ml), neutralized with 1N HCl and then extracted with diethyl ether (80 ml). The organic portion is washed with water (2×60 ml), dried (Na2SO4) and concentrated in vacuo to yield the titled compound as orange crystals. [MH+CH3CN]+=188)

1. additionis added dropwise
2. stirringStirring
3. waitcontinues for a further 2 hours
4. customafter which time, the reaction mixture is quenched with water (2 ml)
5. temperatureto slowly warm to room temperature
6. additionThe cooled solution is poured onto water (200 ml)
7. extractionextracted with diethyl ether (80 ml)
8. washThe organic portion is washed with water (2×60 ml)
9. dry with materialdried (Na2SO4)
10. concentrationconcentrated in vacuo

ORD record

ord-0788c2dfd66a40c28b7cd952ec7c6b6a

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07666878B2