6-Bromopyridine-2-carboxylic acid → 6-(2-Fluorophenyl)pyridine-2-carboxylic acid

HRID 1523488Notes

Reaction equation

HRID 1523488 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=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:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5939196-Bromopyridine-2-carboxylic acidHCID 27343542-Fluorophenylboronic acid

Product 1

HCID 247301386-(2-Fluorophenyl)pyridine-2-carboxylic acidYield 93%

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

Method 1 was followed using 6-bromopicolinic acid (1.0 equiv.) and 2-fluorophenylboronic acid (1.5 equiv.) and Pd(dppf)Cl2-DCM (0.05 equiv.) to give 6-(2-fluorophenyl)picolinic acid in 93% yield. LC/MS=218.0 (M+H), Rt=0.66 min.

Sources & evidence

ORD record
ord-ab4f494e4dc3470fad69816e8597595e
Source dataset
uspto-grants-2015_07
Patent number
US09079889B2

Reaction notes

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