Reaction #2069961

Reaction equation

2-chloro-3-aminopyridine

tetrahydrofuran

ethyl acetate

1-chloropyrrolopyridine

→

title compound

7-(4-Butylbenzyl)-1H-pyrrolo[2,3-c]pyridine

Conditions

Workup

1. 1
   Temperaturecooling
2. 2
   Temperaturewhile heating
3. 3
   Temperatureunder reflux for 4 hours
4. 4
   WashThe resulting mixture was washed with a saturated aqueous ammonium chloride solution and saturated brine
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   OtherThe residue was purified by silica gel column chromatography

Procedure

The compound of Example B205 (800 μl, 0.3 mmol) was added to a solution of 1-chloropyrrolopyridine (19.4 mg, 0.127 mmol), which was synthesized from 2-chloro-3-aminopyridine according to the method of H07-165,708A, and dichloro(diphenylphosphinopropane)nickel (6.9 mg, 0.013 mmol) in tetrahydrofuran (1 ml) under ice-cooling, and the mixture was stirred while heating under reflux for 4 hours. After allowing the mixture to cool to room temperature, ethyl acetate was added thereto. The resulting mixture was washed with a saturated aqueous ammonium chloride solution and saturated brine, then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (7.1 mg).

Source