Phenylboronic Acid → Methyl 2-(benzyloxy)-6-phenylisonicotinate

HRID 1096956Notes

Reaction equation

HRID 1096956 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].[K+].Cl[C:13]1[CH:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=[C:15]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:14]=1>CC([O-])=O.CC([O-])=O.[Pd+2].C1COCC1>[C:1]1([C:13]2[CH:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=[C:15]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 66827Phenylboronic AcidHCID 522689Potassium FluorideHCID 57930944Methyl 2-(benzyloxy)-6-chloroisonicotinate

Product 1

HCID 57930997Methyl 2-(benzyloxy)-6-phenylisonicotinate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Phenylboronic acid (3.4 g), Pd(OAc)2 (528 mg), tBu2-P-Ph-Ph (1.4 g) and potassium fluoride (4.1 g) were added in that order to a THF (200 mL) solution of methyl 2-chloro-6-benzyloxypyridine-4-carboxylate (6.5 g), and stirred overnight at 50° C. The reaction liquid was filtered through Celite, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound as a yellow oil.

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered through Celite
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6eb487ceb3cc4fd3a1d68e5d1f7d8052
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

Loading…