2-Fluorophenylboronic acid → 3-Fluoro-6-(2-fluorophenyl)picolinic acid

HRID 2192624Notes

Reaction equation

HRID 2192624 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[C:5]([F:11])=[CH:4][CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[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:11][C:5]1[C:6]([C:8]([OH:10])=[O:9])=[N:7][C:2]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[F:12])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 27343542-Fluorophenylboronic acidHCID 707008736-Bromo-3-fluoropyridine-2-carboxylic acid

Product 1

HCID 463139033-Fluoro-6-(2-fluorophenyl)picolinic acidYield 81%

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

Method 1 was followed using 6-bromo-3-fluoropicolinic acid (1.0 equiv.) and 2-fluorophenylboronic acid (1.5 equiv.) and Pd(dppf)Cl2-DCM (0.05 equiv.) to give 3-fluoro-6-(2-fluorophenyl)picolinic acid in 81% yield. LC/MS=236.1 (M+H), Rt=0.72 min.

Sources & evidence

ORD record
ord-b30d6cfbf7b547a8ad7bb9c5d665482c
Source dataset
uspto-grants-2012_12
Patent number
US08329732B2

Reaction notes

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