3,4-Difluorobenzeneboronic acid → 6-(3,4-Difluorophenyl)-5-fluoropicolinic acid

HRID 1523484Notes

Reaction equation

HRID 1523484 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[F:11].[F:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][C:18]=1[F:19]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[F:12][C:13]1[CH:14]=[C:15]([C:2]2[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=2[F:11])[CH:16]=[CH:17][C:18]=1[F:19]

Participants

4

Reactant 2

HCID 27343373,4-Difluorobenzeneboronic acidHCID 534011946-Bromo-5-fluoropicolinic Acid

Product 1

HCID 592264686-(3,4-Difluorophenyl)-5-fluoropicolinic acidYield 70%

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

Method 1 was followed using 6-bromo-5-fluoropicolinic acid (1.0 equiv.) and 3,4-difluorophenylboronic acid (1.3 equiv.) and Pd(dppf)Cl2-DCM (0.05 equiv.) to give 6-(3,4-difluorophenyl)-5-fluoropicolinic acid in 70% yield. LC/MS=254.1 (M+H), Rt=0.81 min.

Sources & evidence

ORD record
ord-48079fddfc334e16909d8886f6ec7f45
Source dataset
uspto-grants-2015_07
Patent number
US09079889B2

Reaction notes

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