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

HRID 1712926Notes

Reaction equation

HRID 1712926 reaction equation
OB(O)[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)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:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 79732-BromopyridineHCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 8216924-(2-Pyridyl)Benzoic AcidYield 85.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-(dihydroxyboryl)benzoic acid (1.03 g, 6.21 mmol) and 2-bromopyridine (0.59 mL, 6.21 mmol) in ACN (20 mL) was added sodium carbonate (0.396 g, 3.74 mmol) in water (20 mL). The reaction mixture was degassed with argon and then tetrakis(triphenylphosphine)palladium (0.108 g, 0.09 mmol) was added. The reaction mixture was allowed to stir at 90° C. overnight and then filtered. The solution was concentrated to remove ACN and the aqueous solution was washed with DCM. The aqueous solution was acidified with 1N HCl and the resulting white precipitate was filtered and dried to give 4-pyridin-2-ylbenzoic acid (1.06 g, 85%). LCMS: (FA) ES+ 200.1.

Workup

  1. customThe reaction mixture was degassed with argon
  2. filtrationfiltered
  3. concentrationThe solution was concentrated
  4. customto remove ACN
  5. washthe aqueous solution was washed with DCM
  6. filtrationthe resulting white precipitate was filtered
  7. customdried

Sources & evidence

ORD record
ord-f0d34c4fb2314a98b0b64f94fc212818
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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