Ethanol → Methyl 2-(4-fluorophenyl)nicotinate

HRID 1251913Notes

Reaction equation

HRID 1251913 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 819931Methyl 2-chloronicotinate

Product 1

HCID 15318001Methyl 2-(4-fluorophenyl)nicotinate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 2-chloropyridin-3-carboxylate (6.8 g.), 4-fluorobenzeneboronic acid (7.2 g.), 1M. aqueous sodium carbonate (40 ml.), Pd(dppb)Cl2(1.2 g.), ethanol(10 ml.) and toluene(150 ml.) was stirred at reflux under an inert atmosphere for 5 hr. The reaction was then cooled, the oganic layer separated, the aqueous extracted with toluene and then the Icombined extracts dried and evaporated to dryness. The product was purified by flash column chromatography eluting wth ethyl acetate/iso-hexane(9:1,8:2,7:3) to give methyl 2-(4-fluorophenyl)pyridin-3-carboxylate as a white solid(7.5 g.)

Workup

  1. temperatureat reflux under an inert atmosphere for 5 hr
  2. temperatureThe reaction was then cooled
  3. customthe oganic layer separated
  4. extractionthe aqueous extracted with toluene
  5. customthe Icombined extracts dried
  6. customevaporated to dryness
  7. customThe product was purified by flash column chromatography
  8. washeluting wth ethyl acetate/iso-hexane(9:1,8:2,7:3)

Sources & evidence

ORD record
ord-9b0790c2e50f4fad9f8d512fe849c86c
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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