Dimethylformamide → 4-Bromo-1-(oxan-4-yl)-1H-pyrazole

HRID 1425967Notes

Reaction equation

HRID 1425967 reaction equation
[Br:1][C:2]1N=[N:4][NH:5][CH:6]=1.[O:7]1[CH2:12][CH2:11][CH:10](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:9][CH2:8]1.[C:24](=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>O>[Br:1][C:2]1[CH:24]=[N:4][N:5]([CH:10]2[CH2:11][CH2:12][O:7][CH2:8][CH2:9]2)[CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 13961807Tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonateHCID 1784194684-Bromo-2H-1,2,3-triazole

Product 1

HCID 510639264-Bromo-1-(oxan-4-yl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-bromo-triazole (0.30 g), toluene-4-sulfonic acid tetrahydro-pyran-4-yl ester (0.52 g), cesium carbonate (1.00 g), and N,N-dimethylformamide (7 mL) was stirred at 60° C. overnight. After cooling to ambient temperature, water was added and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), and concentrated. The residue was triturated with cyclohexane/diethyl ether to afford the title compound as a colorless solid. Yield: 0.26 g (55% of theory); LC (method 3): tR=2.75 min; Mass spectrum (ESI+): m/z=231/233 (Br) [M+H]+.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was triturated with cyclohexane/diethyl ether

Sources & evidence

ORD record
ord-e5f2a16cd9eb4ef0a6149ae69b29e3ef
Source dataset
uspto-grants-2015_01
Patent number
US08933072B2

Reaction notes

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