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

HRID 876807Notes

Reaction equation

CS(O[CH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)(=O)=O.[Br:12][C:13]1[CH:14]=[N:15][NH:16][CH:17]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>>[Br:12][C:13]1[CH:14]=[N:15][N:16]([CH:6]2[CH2:11][CH2:10][O:9][CH2:8][CH2:7]2)[CH:17]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 11430Potassium Carbonate

HCID 163754-Bromopyrazole

HCID 11344352Oxan-4-yl methanesulfonate

Product 1

HCID 510639264-Bromo-1-(oxan-4-yl)-1H-pyrazoleYield 37.3%

Conditions

Temperature: 80 °C

Procedure

The mixture of tetrahydro-2H-pyran-4-yl methanesulfonate (U-2) (1.8 g, 10 mmol), 4-bromo-1H-pyrazole (1.46 g, 10 mmol) and K2CO3(1.4 g, 10 mmol) in DMF (10 mmol) was stirred at 80° C. overnight, then purified by chromatography to afford the title compound (861 mg). MS (m/z): 231 (M+1)+.

Workup

custompurified by chromatography

Sources & evidence

ORD record: ord-2e3478ea3f884500847c8e4d2324601c
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987269B2

Reaction notes

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