6-Bromopyridine-2-carboxylic acid → 6-(2-Fluoro-5-propoxyphenyl)picolinic acid

HRID 1523491Notes

Reaction equation

HRID 1523491 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][C:15]([O:18][CH2:19][CH2:20][CH3:21])=[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][C:15]([O:18][CH2:19][CH2:20][CH3:21])=[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 16217464(2-Fluoro-5-propoxyphenyl)boronic acid

Product 1

HCID 592265896-(2-Fluoro-5-propoxyphenyl)picolinic acidYield 20%

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

Method 1 was followed using 6-bromopicolinic acid (1.0 equiv.) and 2-fluoro-5-propoxyphenylboronic acid (1.5 equiv.) and Pd(dppf)Cl2-DCM (0.15 equiv.) to give 6-(2-fluoro-5-propoxyphenyl)picolinic acid in 20% yield. LC/MS=276.0 (M+H), Rt=0.87 min.

Sources & evidence

ORD record
ord-b5297998bdd145089fe0cc8c49a5e4e2
Source dataset
uspto-grants-2015_07
Patent number
US09079889B2

Reaction notes

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