1-Cyclohexenylboronic acid → HCID 59226617, compound

HRID 2192630Notes

Reaction equation

HRID 2192630 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].[C:12]1(B(O)O)[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=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>[C:12]1([C:2]2[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=2[F:11])[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=1

Participants

4

Reactant 2

HCID 38629021-Cyclohexenylboronic acidHCID 534011946-Bromo-5-fluoropicolinic Acid

Product 1

HCID 59226617HCID 59226617, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

Method 1 was followed using 6-bromo-5-fluoropicolinic acid (1.0 equiv.) and cyclohexenylboronic acid (1.3 equiv.) and Pd(dppf)Cl2-DCM (0.15 equiv.) to give 6-cyclohexenyl-5-fluoropicolinic acid in 61% yield. LC/MS=222.0 (M+H), Rt=0.52 min.

Sources & evidence

ORD record
ord-fc5b06c73baf4b1fbf410323251a68be
Source dataset
uspto-grants-2012_12
Patent number
US08329732B2

Reaction notes

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