Potassium Carbonate → Methyl 3-phenylpicolinate

HRID 1099194Notes

Reaction equation

HRID 1099194 reaction equation
FC(F)(F)S(O[C:7]1[C:8]([C:13]([O:15][CH3:16])=[O:14])=[N:9][CH:10]=[CH:11][CH:12]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:25]1([C:7]2[C:8]([C:13]([O:15][CH3:16])=[O:14])=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 11066008Methyl 3-(trifluoromethylsulfonyloxy)-pyridine-2-carboxylate

Product 1

HCID 11063767Methyl 3-phenylpicolinateYield 79.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of methyl 3-{[(trifluoromethyl)sulfonyl]oxy}pyridine-2-carboxylate (148.6 g, 521 mmol) in anhydrous toluene (550 ml) were added potassium carbonate (148.6 g), tetrakis(triphenylphosphine)palladium(0) (6 g), and phenyl boronic acid (70 g, 574 mmol). The reaction was equipped with a mechanical stirring apparatus and heated to reflux for 2 h. The reaction suspension was filtered through a bed of celite and washed with EtOAc. The filtrate was concentrated in vacuo and purified via flash chromatography (silica, 20% EtOAc/hexanes isocratic) to provide methyl 3-phenylpyridine-2-carboxylate (88.5 g).

Workup

  1. customThe reaction was equipped with a mechanical stirring apparatus
  2. temperatureheated
  3. temperatureto reflux for 2 h
  4. filtrationThe reaction suspension was filtered through a bed of celite
  5. washwashed with EtOAc
  6. concentrationThe filtrate was concentrated in vacuo
  7. custompurified via flash chromatography (silica, 20% EtOAc/hexanes isocratic)

Sources & evidence

ORD record
ord-3171a615d8104a19b9c234f5bf490b67
Source dataset
uspto-grants-2012_03
Patent number
US08143405B2

Reaction notes

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