Pyrazole → tert-butyl-3-(1H-pyrazol-1-yl)benzylcarbamate

HRID 513297

Reaction equation

HRID 513297 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](I)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].CN[C@H]1CCCC[C@@H]1NC.[NH:27]1[CH:31]=[CH:30][CH:29]=[N:28]1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.CS(C)=O.[Cu]I>[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N:27]2[CH:31]=[CH:30][CH:29]=[N:28]2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 11645663tert-Butyl 3-iodobenzylcarbamateHCID 13822957(1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamine

Product 1

HCID 56791985tert-butyl-3-(1H-pyrazol-1-yl)benzylcarbamateYield 70.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of tert-butyl-3-iodobenzylcarbamate (550 mg, 1.65 mmol) in Dioxane (1.2 mL) and DMSO (1.2 mL) was added CuI (16 mg, 0.083 mmol), (1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine (0.052 ml, 0.33 mmol), pyrazole (135 mg, 1.98 mmol) and K2CO3 (479 mg, 3.47 mmol). After stirring at 120° C. for 3 h, it was concentrated and the residue was purified by column chromatography to give tert-butyl-3-(1H-pyrazol-1-yl)benzylcarbamate (317 mg).

Workup

  1. concentrationit was concentrated
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-953510000c43469085ac5217a1dfbbdd
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Linked notes

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