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

HRID 2202006Notes

Reaction equation

HRID 2202006 reaction equation
B([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)(O)O.Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 8216924-(2-Pyridyl)Benzoic AcidYield 41.8%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 4-boronobenzoic acid (200 mg, 1.2 mmol), 2-bromopyridine (208 mg, 1.3 mmol), K2CO3 (497 mg, 3.6 mmol) and Pd(dppf)Cl2 (10 mg) in dioxane (4 mL) and H2O (1 mL) was stirred at 125° C. for 30 min with microwave heating under N2. The catalyst was filtered, and the filtrate was acidified with 2N HCl to pH 5-6. The solution was concentrated, and the residue was dissolved in MeOH and filtered. The filtrate was concentrated, and the residue was purified by prep-TLC to give the title compound (100 mg, Yield 41.8%). LCMS (m/z): 200.1 (M+1).

Workup

  1. temperatureheating under N2
  2. filtrationThe catalyst was filtered
  3. concentrationThe solution was concentrated
  4. dissolutionthe residue was dissolved in MeOH
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-e93773ef09b341bca9b38f11a4415a2c
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

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