(2-Fluoro-5-propoxyphenyl)boronic acid → 5-Fluoro-6-(2-fluoro-5-propoxyphenyl)picolinic acid

HRID 1523487Notes

Reaction equation

HRID 1523487 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]([O:19][CH2:20][CH2:21][CH3:22])=[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:3]1[CH:4]=[CH:5][C:6]([C:8]([OH:10])=[O:9])=[N:7][C:2]=1[C:18]1[CH:17]=[C:16]([O:19][CH2:20][CH2:21][CH3:22])[CH:15]=[CH:14][C:13]=1[F:12]

Participants

4

Reactant 2

HCID 16217464(2-Fluoro-5-propoxyphenyl)boronic acidHCID 534011946-Bromo-5-fluoropicolinic Acid

Product 1

HCID 592264725-Fluoro-6-(2-fluoro-5-propoxyphenyl)picolinic acid

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

Method 1 was followed using 6-bromo-5-fluoropicolinic acid (1.0 equiv.) and 2-fluoro-5-propoxyphenylboronic acid (1.5 equiv.) and Pd(dppf)Cl2-DCM (0.05 equiv.) to give 5-fluoro-6-(2-fluoro-5-propoxyphenyl)picolinic acid. LC/MS=294.2 (M+H), Rt=0.95 min.

Sources & evidence

ORD record
ord-11352226f94e4ea697180e9171e198f0
Source dataset
uspto-grants-2015_07
Patent number
US09079889B2

Reaction notes

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