Potassium Carbonate → 4-(Pyridin-4-yl)benzoic acid

HRID 2185018Notes

Reaction equation

HRID 2185018 reaction equation
Cl.Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.CC1(C)C(C)(C)OB([C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=2)O1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.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>[N:6]1[CH:7]=[CH:8][C:3]([C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=2)=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 881004-Bromopyridinium chlorideHCID 27346214-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

Product 1

HCID 15208114-(Pyridin-4-yl)benzoic acidYield 65.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-Bromopyridine hydrochloride (0.4 g, 2 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (0.5 g, 2 mmol), and tetrakis(triphenylphosphine)palladium(0) (50 mg, 0.04 mmol) in dimethylformamide (15 mL) was treated with 2M potassium carbonate (2 mL) and the mixture was heated to 80° C. for 16 h. The mixture was concentrated in vacuo and the residue was diluted with water to afford a solid which was filtered to afford the title compound (0.26 g).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue was diluted with water
  3. customto afford a solid which
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-2c9b561b32c24dc7bd0eb70f61523f77
Source dataset
uspto-grants-2002_06
Patent number
US06399656B1

Reaction notes

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