2-Bromopyridine → 2-(Pyridin-2-YL)benzoic acid

HRID 2202004Notes

Reaction equation

HRID 2202004 reaction equation
B([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])(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][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

7

Reactant 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 27339852-(Dihydroxyboranyl)benzoic acid

Product 1

HCID 157331752-(Pyridin-2-YL)benzoic acidYield 42.9%

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 2-boronobenzoic acid (400 mg, 2.4 mmol), 2-bromopyridine (416 mg, 2.6 mmol), K2CO3 (994 mg, 7.2 mmol) and Pd(dppf)Cl2 (20 mg) in dioxane (8 mL) and H2O (2 mL) was stirred at 125° C. for 30 min. under 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 (205 mg, Yield 42.9%). LCMS (m/z): 200.0 (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-e619df9a22ba451985323d43e28d9a63
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

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