Water → HCID 67084484, compound

HRID 595199

Reaction equation

HRID 595199 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[Br:7][C:8]1[CH:9]=[N:10][NH:11][CH:12]=1.Cl[CH2:14][CH:15]1[CH2:19][O:18][C:17]([CH3:21])([CH3:20])[O:16]1.O>CN(C=O)C.CCOC(C)=O>[Br:7][C:8]1[CH:9]=[N:10][N:11]([CH2:14][CH:15]2[CH2:19][O:18][C:17]([CH3:21])([CH3:20])[O:16]2)[CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 163754-BromopyrazoleHCID 203744-(Chloromethyl)-2,2-dimethyl-1,3-dioxolane

Product 1

HCID 67084484HCID 67084484, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

Cs2CO3 (5.3 g, 16.3 mmol) was added to a solution of 4-bromo-1H-pyrazole (2 g, 13.6 mmol) in DMF (10 mL), followed by 4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane (2.46 g, 16.3 mmol) and the resulting mixture heated to an internal temperature of 65° C. After stirring for 14 h, water and EtOAc was added and the layers separated. The organic layer was washed a second time with water, dried with over anhydorus magnesium sulfate, filtered and concentrated under reduced pressure. The resulting crude residue was absorbed on silica gel and purified by column chromatography on silica (0 to 100% EtOAc/Hex) to afford 4-bromo-1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazole as a light yellow oil, MS ESI calcd. for C9H14BrN2O2 [M+H]+ 261. found 261.

Workup

  1. customthe layers separated
  2. washThe organic layer was washed a second time with water
  3. dry with materialdried with over anhydorus magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude residue was absorbed on silica gel
  7. custompurified by column chromatography on silica (0 to 100% EtOAc/Hex)

Sources & evidence

ORD record
ord-ab9489696be3469d873d56cce9da4507
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Linked notes

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