4-Benzyloxy-2-fluorophenylboronic acid → 6-(4-(Benzyloxy)-2-fluorophenyl)-3-fluoropicolinic acid

HRID 2046856Notes

Reaction equation

HRID 2046856 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.[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])[C:5]([F:11])=[CH:4][CH:3]=2)=[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 707008736-Bromo-3-fluoropyridine-2-carboxylic acid

Product 1

HCID 592265166-(4-(Benzyloxy)-2-fluorophenyl)-3-fluoropicolinic acidYield 41%

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

Method 1 was followed using 6-bromo-3-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)-3-fluoropicolinic acid in 41% yield. LC/MS=342.1 (M+H), Rt=1.06 min.

Sources & evidence

ORD record
ord-3a6c28bd30e040a0a8381c4ced57a99b
Source dataset
uspto-grants-2013_11
Patent number
US08592455B2

Reaction notes

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