Pyrazole → 4'-Methyl-5-pyrazol-1-yl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide

HRID 2091825Notes

Reaction equation

HRID 2091825 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([NH:6][C:7]([C:9]1[CH:10]=[C:11]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[CH:12]=[C:13](I)[CH:14]=1)=[O:8])[CH3:5].[NH:23]1[CH:27]=[CH:26][CH:25]=[N:24]1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C.[Cu]I>[CH3:1][O:2][CH2:3][CH:4]([NH:6][C:7]([C:9]1[CH:10]=[C:11]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[CH:12]=[C:13]([N:23]2[CH:27]=[CH:26][CH:25]=[N:24]2)[CH:14]=1)=[O:8])[CH3:5]

Participants

8

Reactant 4

HCID 1048PyrazoleHCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 594325375-Iodo-4'-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide

Product 1

HCID 577706434'-Methyl-5-pyrazol-1-yl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 5-iodo-4′-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide (0.15 g, 0.367 mmol) in 1 ml DMF was added pyrazole (0.062 g, 0.917 mmol), CuI (0.03667 mmol), 1,10-phenanthroline (0.0734 mmol) and Cs2CO3 (0.734 mmol). The mixture was subjected to microwave irridation at 150° C. for 45 minutes. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC to give 4′-Methyl-5-pyrazol-1-yl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide, MS (M+H)=350.

Workup

  1. customat 150° C.
  2. customfor 45 minutes
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b5231e0eb4a048039023d9a10d475691
Source dataset
uspto-grants-2013_05
Patent number
US08440673B2

Reaction notes

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