Reaction #59077

Reaction equation

2-bromo-1-chloro-4-nitrobenzene

3-fluoropyridin-4-yl-4-boronic acid

sodium carbonate

→

4-(2-chloro-5-nitrophenyl)-3-fluoropyridine

Solvents

DME H2O

Conditions

Workup

1. 1
   Otherwas degassed with N2 for one half hour
2. 2
   Otherdegassed for another 10 minutes
3. 3
   OtherReaction
4. 4
   Concentrationthen concentrated
5. 5
   Otherpartitioned between ethyl acetate and water
6. 6
   WashOrganic layer washed with brine
7. 7
   Dryingdried over sodium sulfate
8. 8
   Concentrationconcentrated
9. 9
   OtherPurification on silica gel, 10% ethyl acetate in hexanes

Procedure

A mixture of DME: H2O (3:1) was degassed with N2 for one half hour. 2-bromo-1-chloro-4-nitrobenzene (1 eq) added and degassed for another 10 minutes. 1,1′-bis(diphenylphosphino)ferrocene palladium(II)chloride (0.05 eq), 3-fluoropyridin-4-yl-4-boronic acid (1 eq), and sodium carbonate (3 eq) were then added and stirred at 100° C. for 16 hours. Reaction then concentrated and partitioned between ethyl acetate and water. Organic layer washed with brine, dried over sodium sulfate and concentrated. Purification on silica gel, 10% ethyl acetate in hexanes to yield 4-(2-chloro-5-nitrophenyl)-3-fluoropyridine. HPLC=4.57 min; MS: MH+=253.

Source