Cesium carbonate → 4-(3-methyl-5-nitrophenyl)-1-(2-methylallyl)-1H-pyrazole

HRID 595159Notes

Reaction equation

Br[CH2:2][C:3]([CH3:5])=[CH2:4].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:12][C:13]1[CH:14]=[C:15]([C:22]2[CH:23]=[N:24][NH:25][CH:26]=2)[CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=1>CC(N(C)C)=O>[CH3:12][C:13]1[CH:14]=[C:15]([C:22]2[CH:26]=[N:25][N:24]([CH2:4][C:3]([CH3:5])=[CH2:2])[CH:23]=2)[CH:16]=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=1

Participants

Conditions

Temperature: 70 °C

Procedure

3-Bromo-2-methylprop-1-ene (4.19 g, 31.0 mmol) and cesium carbonate (13.5 g, 41.3 mmol) were added to a solution of 4-(3-methyl-5-nitrophenyl)-1H-pyrazole (4.20 g, 20.7 mmol) in dimethylacetamide (41 mL) and stirred at 70° C. for 18 h. The mixture was allowed to cool to room temperature, passed through CELITE, washed with methanol, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-50% EtOAc/Hexane) to afford 4-(3-methyl-5-nitrophenyl)-1-(2-methylallyl)-1H-pyrazole. MS ESI calc'd. for C14H16N3O2 [M+H]+ 258. found 258.

Workup

temperatureto cool to room temperature
washwashed with methanol
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel (0-50% EtOAc/Hexane)

Sources & evidence

ORD record: ord-84596afe64144a46aed622af34e3e185
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242984B2

Reaction notes

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