N-bromobutanimide → tert-Butyl 3-(4-bromo-1-methyl-1H-pyrazol-5-yl)piperidine-1-carboxylate

HRID 1530604Notes

Reaction equation

HRID 1530604 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]2[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]2)=[CH:5][CH:4]=[N:3]1.C1C(=O)N([Br:27])C(=O)C1>C1COCC1>[Br:27][C:5]1[CH:4]=[N:3][N:2]([CH3:1])[C:6]=1[CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 68313066tert-butyl 3-(1-methyl-1H-pyrazol-5-yl)piperidine-1-carboxylate

Product 1

HCID 68313245tert-Butyl 3-(4-bromo-1-methyl-1H-pyrazol-5-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 3-(1-methyl-1H-pyrazol-5-yl)piperidine-1-carboxylate (680 mg, 2.50 mmol) in THF (20 mL) was added NBS (486 mg, 2.80 mmol). The reaction mixture was stirred for 2 h. After concentration, the residue was purified by silica gel chromatography eluting with a 0-50% gradient of EtOAc in petroleum ether to give tert-butyl

Workup

  1. concentrationAfter concentration
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with a 0-50% gradient of EtOAc in petroleum ether
  4. customto give tert-butyl

Sources & evidence

ORD record
ord-def8965d9181484ebd0f93846268d550
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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