Pyrazole → methyl 2-fluoro-4-(1H-pyrazol-1-yl)benzoate

HRID 629406Notes

Reaction equation

HRID 629406 reaction equation
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9].[NH:15]1[CH:19]=[CH:18][CH:17]=[N:16]1>CO.[Cu-]=O>[F:1][C:2]1[CH:3]=[C:4]([N:15]2[CH:19]=[CH:18][CH:17]=[N:16]2)[CH:5]=[CH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 2

HCID 1048PyrazoleHCID 27828183-Fluoro-4-(methoxycarbonyl)benzeneboronic acid

Product 1

HCID 118468121methyl 2-fluoro-4-(1H-pyrazol-1-yl)benzoateYield 33.3%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (3-fluoro-4-(methoxycarbonyl)phenyl)boronic acid (2.40 g) and 1H-pyrazole (0.99 g) in methanol (54.0 mL) was added copper(I) oxide (0.10 g), and the mixture was stirred overnight at 50° C. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.89 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f8d42bce7e9b49cabd899a17a199b142
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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