(2,5-Difluorophenyl)boronic acid → HCID 59226541, compound

HRID 2192616Notes

Reaction equation

HRID 2192616 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:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1B(O)O>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:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[F:11]

Participants

4

Reactant 2

HCID 2734335(2,5-Difluorophenyl)boronic acidHCID 534011946-Bromo-5-fluoropicolinic Acid

Product 1

HCID 59226541HCID 59226541, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

Method 1 was followed using 6-bromo-5-fluoropicolinic acid (1.0 equiv.) and 2,5-difluorophenylboronic acid (1.3 equiv.) and Pd(dppf)Cl2-DCM (0.05 equiv.) to give 6-(2,5-difluorophenyl)-5-fluoropicolinic acid in 80% yield. LC/MS=254.1 (M+H), Rt=0.74 min.

Sources & evidence

ORD record
ord-deba1ddbbec94457a102d3bf77c901bc
Source dataset
uspto-grants-2012_12
Patent number
US08329732B2

Reaction notes

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