4-Bromopyrazole → HCID 67027251, compound

HRID 1465715Notes

Reaction equation

HRID 1465715 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[H-].[Na+].CS(O[CH:14]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1)(=O)=O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH:18]2[CH2:19][CH2:14][CH2:15][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17]2)[CH:6]=1

Participants

5

Reactant 3

HCID 163754-BromopyrazoleHCID 24758Sodium hydrideHCID 568122N-Boc-3-mesyloxypiperidine

Product 1

HCID 67027251HCID 67027251, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-Bromopyrazole (2.94 g, 20 mmol) dissolved in DMF (20 mL) was cooled to 0° C., sodium hydride (900 mg, 22.5 mmol) was added portion-wise over 1 h. After warmed to room temperature and stirred for 1 h, tert-butyl 3-(methylsulfonyloxy)-piperidine-1-carboxylate (5.03 g, 20 mmol) was added, and the reaction mixture was heated at 100° C. overnight. The reaction mixture was quenched with saturated NH4Cl, and extracted with EtOAc. The organic layer was washed with H2O, brine, dried and concentrated. Crude mixture was column purified with mixture of EtOAc and hexane to give tert-butyl 3-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylate (1.97 g) as white solid.

Workup

  1. temperatureAfter warmed to room temperature
  2. temperaturethe reaction mixture was heated at 100° C. overnight
  3. customThe reaction mixture was quenched with saturated NH4Cl
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with H2O, brine
  6. customdried
  7. concentrationconcentrated
  8. custompurified with mixture of EtOAc and hexane

Sources & evidence

ORD record
ord-b04695eb6dbc4c6a8499c1d35b1a15ee
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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