Reaction #743684

Reaction equation

3-cyanomethyl-4-iodo-benzonitrile

lithium chloride

magnesium

lithium chloride

isopropyl chloride

isopropylmagnesium chloride

copper (I) cyanide

lithium chloride

6,7-dihydro-5H-imidazo[1,5-a]pyridine-8-one

→

3-Cyanomethyl-4-(8-hydroxy-5,6,7,8-tetrahydro-imidazo[1,5-a]pyridin-8-yl)-benzonitrile

Solvents

tetrahydrofuran

THF

Conditions

Workup

1. 1
   OtherIn a dried flask under Ar atmosphere are placed
2. 2
   workup.STIRRINGThe reaction mixture is stirred for 1 hour at 0° C.
3. 3
   Otherquenched by addition of aqueous saturated ammonium chloride solution
4. 4
   Extractionextracted with diethyl ether (3×)
5. 5
   WashThe combined organic phases are washed with brine
6. 6
   Dryingdried with sodium sulphate
7. 7
   Otherevaporated

Procedure

In a dried flask under Ar atmosphere are placed 1.05 mmol of isopropylmagnesium chloride.lithium chloride in tetrahydrofuran solution (prepared from magnesium, dry lithium chloride and isopropyl chloride in THF according to A. Krasovskiy and P. Knochel; Angewandte Chemie International Edition 2004, 43, 3333-3336). The solution is cooled to −15° C. and 1 mmol of 3-cyanomethyl-4-iodo-benzonitrile is added in one portion. The reaction mixture is stirred for 15 minutes at −10° C. and 0.02 ml of a copper (I) cyanide.2 lithium chloride solution (10M in tetrahydrofuran) as well as 1.1 mmol of 6,7-dihydro-5H-imidazo[1,5-a]pyridine-8-one [426219-51-4] are added. The reaction mixture is stirred for 1 hour at 0° C., then quenched by addition of aqueous saturated ammonium chloride solution and extracted with diethyl ether (3×). The combined organic phases are washed with brine, dried with sodium sulphate and evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60F) on the basis of the Rf value.

Source