2-Fluorophenylboronic acid → Methyl 3-amino-5-fluoro-6-(2-fluorophenyl)picolinate

HRID 1523480Notes

Reaction equation

HRID 1523480 reaction equation
[NH2:1][C:2]1[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:4][C:5](Br)=[C:6]([F:8])[CH:7]=1.[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=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>[NH2:1][C:2]1[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:4][C:5]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[F:14])=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 27343542-Fluorophenylboronic acidHCID 72698878Methyl 3-amino-6-bromo-5-fluoropicolinate

Product 1

HCID 59226575Methyl 3-amino-5-fluoro-6-(2-fluorophenyl)picolinateYield 99%

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

Method 1 was followed using methyl 3-amino-6-bromo-5-fluoropicolinate (1.0 equiv.) and 2-fluoro-phenylboronic acid (1.5 equiv.) and Pd(dppf)Cl2-DCM (0.05 equiv.) to give methyl 3-amino-5-fluoro-6-(2-fluorophenyl)picolinate in >99% yield. LC/MS=265.0 (M+H), Rt=0.77 min.

Sources & evidence

ORD record
ord-a95d6e9e35984f7790a1a55dc6292199
Source dataset
uspto-grants-2015_07
Patent number
US09079889B2

Reaction notes

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