2-Bromopyridine → 4-(2-Pyridyl)Benzoic Acid

HRID 2244276Notes

Reaction equation

HRID 2244276 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)([OH:3])=[O:2].Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:7]1[CH:8]=[CH:9][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 79732-BromopyridineHCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 8216924-(2-Pyridyl)Benzoic AcidYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 4-carboxybenzeneboronic acid (0.660 g, 3.98 mmol) and 2-bromopyridine (0.38 mL, 3.98 mmol) in dry acetonitrile (20 mL) was added 0.4 M aqueous sodium carbonate (20 mL) and mixture purged with nitrogen for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.240 g) was then added and the reaction mixture heated to 90° C. for 20 hours. The hot mixture was filtered through celite and concentrated in vacuo to remove acetonitrile. The resulting aqueous suspension was diluted with water (20 mL), washed with dichloromethane (2×40 mL), and then acidified to pH 6 by the addition of concentrated hydrochloric acid. The resulting white suspension was diluted with water (20 mL), filtered and the solid product dried in vacuo at 50° C. overnight to give the title compound (0.662 g, 84%) as a white solid, m.p. 232-234° C.

Workup

  1. custompurged with nitrogen for 10 minutes
  2. additionTetrakis(triphenylphosphine)palladium(0) (0.240 g) was then added
  3. filtrationThe hot mixture was filtered through celite and
  4. concentrationconcentrated in vacuo
  5. customto remove acetonitrile
  6. additionThe resulting aqueous suspension was diluted with water (20 mL)
  7. washwashed with dichloromethane (2×40 mL)
  8. additionacidified to pH 6 by the addition of concentrated hydrochloric acid
  9. additionThe resulting white suspension was diluted with water (20 mL)
  10. filtrationfiltered
  11. customthe solid product dried in vacuo at 50° C. overnight

Sources & evidence

ORD record
ord-160765c77b6d47e496ab29c781ce36d8
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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