Ethanol → 5-(3-Fluorophenyl)picolinic acid

HRID 711217Notes

Reaction equation

HRID 711217 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10]C)=[O:9])=[N:6][CH:7]=1.[F:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+].C(O)C>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.C1(C)C=CC=CC=1>[F:12][C:13]1[CH:18]=[C:17]([C:2]2[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=2)[CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 7016458Methyl 5-bromopyridine-2-carboxylate

Product 1

HCID 463131255-(3-Fluorophenyl)picolinic acid

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a round bottom flask was added methyl 5-bromopicolinate 6-5 (900 mg, 4.2 mmol), 3-fluorophenylboronic acid 6-6 (875 mg, 6.3 mmol), Pd(PPh3)4 (482 mg, 0.42 mmol), saturated Na2CO3 (3 mL), ethanol (3 mL) and toluene (9 mL). The reaction was refluxed at 100° C. for 3 hours. The reaction was cooled down to room temperature, and the precipitate was collected by filtration and briefly washed with ethyl acetate. The sodium salt was acidified with 1N HCl to give 5-(3-fluorophenyl)picolinic acid 6-7 as a white solid. MS m/z 218.1 (M+1).

Workup

  1. temperatureThe reaction was cooled down to room temperature
  2. filtrationthe precipitate was collected by filtration
  3. washbriefly washed with ethyl acetate

Sources & evidence

ORD record
ord-cf67ba7c5cd94f73998e4fc4656e7669
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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