4-Benzyloxy-2-fluorophenylboronic acid → 6-(4-(Benzyloxy)-2-fluorophenyl)-5-fluoropicolinic acid

HRID 2192627Notes

Reaction equation

HRID 2192627 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].[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[C:22]([F:29])[CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>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>[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=2[F:11])=[C:22]([F:29])[CH:21]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 27377864-Benzyloxy-2-fluorophenylboronic acidHCID 534011946-Bromo-5-fluoropicolinic Acid

Product 1

HCID 592266186-(4-(Benzyloxy)-2-fluorophenyl)-5-fluoropicolinic acidYield 28%

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

Method 1 was followed using 6-bromo-5-fluoropicolinic acid (1.0 equiv.) and 4-(benzyloxy)-2-fluorophenylboronic acid (1.3 equiv.) and Pd(dppf)Cl2-DCM (0.15 equiv.) to give 6-(4-(benzyloxy)-2-fluorophenyl)-5-fluoropicolinic acid in 28% yield. LC/MS=342.1 (M+H), Rt=1.05 min.

Sources & evidence

ORD record
ord-7fcf8a60de0645589597723bd3eb3121
Source dataset
uspto-grants-2012_12
Patent number
US08329732B2

Reaction notes

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