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

HRID 1822913Notes

Reaction equation

HRID 1822913 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8]([C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1)([OH:10])=[O:9].C([O-])([O-])=O.[Na+].[Na+]>CC#N.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:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:14]1[CH:15]=[CH:16][C:11]([C:8]([OH:10])=[O:9])=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 79732-BromopyridineHCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 8216924-(2-Pyridyl)Benzoic Acid

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

2-Bromopyridine (1.26 g, 7.97 mmol), 4-carboxyphenylboronic acid (1.32 g, 7.95 mmol), and Pd(PPh3)4 (0.48 g, 0.42 mmol) were stirred at 90° overnight in CH3CN (40 mL) and 0.4 M Na2CO3 solution (40 mL, 16 mmol). After this time, the mixture was filtered hot, and the filtrate was concentrated to half-volume under reduced pressure. The remaining liquid was washed with CH2Cl2 (2×20 mL) and then acidified to pH 1 with concentrated HCl. The resulting precipitate was collected by filtration, washed with H2O, and allowed to air-dry to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.74 (m, 1H), 8.19–8.23 (m, 2H), 7.99–8.12(m, 4H), 7.47–7.52 (m, 1H); MS (ESI+) m/z 200 (M+H)+.

Workup

  1. filtrationAfter this time, the mixture was filtered hot
  2. concentrationthe filtrate was concentrated to half-volume under reduced pressure
  3. washThe remaining liquid was washed with CH2Cl2 (2×20 mL)
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with H2O
  6. customto air-dry

Sources & evidence

ORD record
ord-63d1e143a699457aa5ad7dd6f7a30064
Source dataset
uspto-grants-2006_05
Patent number
US07037927B2

Reaction notes

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