Pyrazole → HCID 58314513, compound

HRID 624793Notes

Reaction equation

HRID 624793 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7](I)[CH:6]=[CH:5][C:3]=1[NH2:4].CNCCNC.[NH:16]1[CH:20]=[CH:19][CH:18]=[N:17]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.[Cu]I>[Cl:1][C:2]1[CH:8]=[C:7]([N:16]2[CH:20]=[CH:19][CH:18]=[N:17]2)[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

7

Reactant 4

HCID 1048PyrazoleHCID 8070N,N'-DimethylethylenediamineHCID 10796Cesium carbonateHCID 2829302-Chloro-4-iodoaniline

Product 1

HCID 58314513HCID 58314513, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

2-chloro-4-iodoaniline (760 mg, 3 mmol), N,N′-dimethylethylenediamine (96 μL, 0.9 mmol), 1H-pyrazole (430 mg, 6.3 mmol) were dissolved in DMF (3.8 mL). Cs2CO3 (1.86 g, 5.7 mmol) and CuI (57 mg, 0.3 mmol) were added and the reaction was placed in a 140° C. oil bath. After 3 h, the volatiles were removed in vacuo. The residue was diluted with dichloromethane and purified via flash column chromatography (1% MeOH/dichloromethane) to furnish 2-chloro-4-(1H-pyrazol-1-yl)aniline (540 mg, 93%) as a golden brown oil which crystallized overnight at −20° C.

Workup

  1. customwas placed in a 140° C.
  2. customthe volatiles were removed in vacuo
  3. additionThe residue was diluted with dichloromethane
  4. custompurified via flash column chromatography (1% MeOH/dichloromethane)

Sources & evidence

ORD record
ord-fbcd6159a88e4ddf891708a23dfa4019
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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