2,6-Difluoro-4-methoxybenzeneboronic acid → 6-(2,6-Difluoro-4-methoxyphenyl)-3-fluoropicolinic acid

HRID 1523498Notes

Reaction equation

HRID 1523498 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]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([F:21])[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]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([F:21])[C:14]=1[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[C:5]([F:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 162174242,6-Difluoro-4-methoxybenzeneboronic acidHCID 707008736-Bromo-3-fluoropyridine-2-carboxylic acid

Product 1

HCID 592265566-(2,6-Difluoro-4-methoxyphenyl)-3-fluoropicolinic acidYield 9%

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

Method 1 was followed using 6-bromo-3-fluoropicolinic acid (1.0 equiv.) and 2,6-difluoro-4-methoxyphenylboronic acid (1.3 equiv.) and Pd(dppf)Cl2-DCM (0.15 equiv.) to give 6-(2,6-difluoro-4-methoxyphenyl)-3-fluoropicolinic acid in 9% yield. LC/MS=284.0 (M+H), Rt=0.74 min.

Sources & evidence

ORD record
ord-f6bc87538e0244238a5d865efaa1ad27
Source dataset
uspto-grants-2015_07
Patent number
US09079889B2

Reaction notes

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