2-Fluoro-5-methoxyphenylboronic acid → 3-Fluoro-6-(2-fluoro-5-methoxyphenyl)picolinic acid

HRID 2046853Notes

Reaction equation

HRID 2046853 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][C:16]([O:19][CH3:20])=[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]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:13]=2[F:12])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 41572112-Fluoro-5-methoxyphenylboronic acidHCID 707008736-Bromo-3-fluoropyridine-2-carboxylic acid

Product 1

HCID 592265573-Fluoro-6-(2-fluoro-5-methoxyphenyl)picolinic acidYield 89%

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

Method 1 was followed using 6-bromo-3-fluoropicolinic acid (1.0 equiv.) and 2-fluoro-5-methoxyphenylboronic acid (1.3 equiv.) and Pd(dppf)Cl2-DCM (0.15 equiv.) to give 3-fluoro-6-(2-fluoro-5-methoxyphenyl)picolinic acid in 89% yield. LC/MS=266.1 (M+H), Rt=0.79 min.

Sources & evidence

ORD record
ord-7c0ffc2f9d0e482e9454ab583b28f188
Source dataset
uspto-grants-2013_11
Patent number
US08592455B2

Reaction notes

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