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

HRID 880261

Reaction equation

HRID 880261 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-9c80a45b87834459a401f8590f85ee4e
Source dataset
uspto-grants-2015_03
Patent number
US08993555B2

Linked notes

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