Cesium carbonate → 4-iodo-1-[(4-methoxyphenyl)methyl]-1H-pyrazole

HRID 1466937Notes

Reaction equation

HRID 1466937 reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[CH3:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Br)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[I:1][C:2]1[CH:3]=[N:4][N:5]([CH2:13][C:12]2[CH:15]=[CH:16][C:9]([O:8][CH3:7])=[CH:10][CH:11]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 770224-IodopyrazoleHCID 1650214-Methoxybenzyl bromide

Product 1

HCID 574219364-iodo-1-[(4-methoxyphenyl)methyl]-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Iodo-1H-pyrazole (2.0 g, 10.3 mmol), 4-methoxy-benzyl bromide (3.0 mL, 20.6 mmol), and cesium carbonate (5.0 g, 15.5 mmol) were combined in DMF (20 mL) and stirred at room temperature for 30 minutes. The mixture was subjected to standard aqueous workup, and the crude residue was purified on silica gel (0-20% EtOAc in hexanes) to afford the title compound.

Workup

  1. customthe crude residue was purified on silica gel (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b6a6a096470e47d7beeb2140379f4f82
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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