Cesium carbonate → HCID 118208813, compound

HRID 595210Notes

Reaction equation

HRID 595210 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[Br:7][C:8]1[CH:9]=[N:10][NH:11][CH:12]=1.[CH3:13][C:14]1([CH3:29])[CH2:19][CH:18](OS(C)(=O)=O)[CH2:17][CH2:16][CH:15]1[C:25]([O:27][CH3:28])=[O:26]>CN(C=O)C.O>[Br:7][C:8]1[CH:9]=[N:10][N:11]([CH:18]2[CH2:17][CH2:16][CH:15]([C:25]([O:27][CH3:28])=[O:26])[C:14]([CH3:29])([CH3:13])[CH2:19]2)[CH:12]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 163754-BromopyrazoleHCID 118271620HCID 118271620, compound

Product 1

HCID 118208813HCID 118208813, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Cesium carbonate (2.93 g, 9 mmol) and 4-bromopyrazole (482 mg, 3.3 mmol) were added to a solution of methyl 2,2-dimethyl-4-[(methylsulfonyl)oxy]cyclohexanecarboxylate (0.79 g, 3 mmol) in DMF (10 mL). The mixture was stirred at 80° C. for 16 hours. Then the mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (ethyl acetate/petroleum ether) to give methyl 4-(4-bromo-1H-pyrazol-1-yl)-2,2-dimethylcyclohexanecarboxylate. MS ESI calc'd. for C13H20BrN2O2 [M+H]+ 315 and 317. found 315 and 317. 1H NMR (400 MHz, CDCl3): δ 7.35 (s, 1H), 7.22 (s, 1H), 4.53-4.50 (m, 1H), 3.69 (s, 3H), 2.26-2.18 (m, 1H), 2.06-1.78 (m, 4H), 1.36-1.28 (m, 2H), 1.06 (s, 3H), 0.97 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography on silica gel (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-1e8ff6178702463999ed8fed86d440f2
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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