Reaction #41775

Reaction equation

2-bromo-1-methyl-4-nitrobenzene

3-chloro-4-pyridine boronic acid hydrate

sodium carbonate

→

3-chloro-4-(2-methyl-5-nitrophenyl)pyridine

Solvents

dimethoxyethane

water

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   ConcentrationThe reaction mixture was concentrated
3. 3
   Otherpartitioned between ethyl acetate and water
4. 4
   WashThe organic layer was washed with brine
5. 5
   Dryingdried with sodium sulfate
6. 6
   Concentrationconcentrated
7. 7
   OtherPurification on silica gel

Procedure

Nitrogen was bubbled through a solution of 2-bromo-1-methyl-4-nitrobenzene (1 eq) in dimethoxyethane and water (3:1) for 0.5 h. Bis(diphenylphosphino)ferrocene Palladium(II)chloride (0.05 eq) followed by 3-chloro-4-pyridine boronic acid hydrate (1 eq) and sodium carbonate (3 eq) was added and the mixture was heated to 90° C. for 16 h under nitrogen. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was washed with brine and dried with sodium sulfate and concentrated. Purification on silica gel gave 3-chloro-4-(2-methyl-5-nitrophenyl)pyridine. MS: MH+=248.

Source