Cesium carbonate → HCID 66599684, compound

HRID 1909032Notes

Reaction equation

HRID 1909032 reaction equation
[Br:1][C:2]1[C:3]([CH3:8])=[N:4][NH:5][C:6]=1[CH3:7].C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21]>CC(N(C)C)=O.CCOC(C)=O>[Br:1][C:2]1[C:3]([CH3:8])=[N:4][N:5]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:6]=1[CH3:7]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 769374-bromo-3,5-dimethyl-1H-pyrazoleHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 66599684HCID 66599684, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a stirring suspension of 4-bromo-3,5-dimethyl-1H-pyrazole (3.5 g, 20 mmol) and Cs2CO3 (13 g, 40 mmol) in 40 mL DMA was added (2-chloromethoxy-ethyl)-trimethyl-silane (5.3 mL, 30 mmol) at room temperature. The resulting mixture was stirred for 1 hour and was diluted with 100 mL EtOAc. The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was then purified by SiO2 chromatography (eluting with EtOAc/Heptane system) to give 4-bromo-3,5-dimethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazole 6.1 g (100%). MS(ESI) m/z 307.3 (M+H)+. Step 2 was performed using General procedure L (Suzuki) to give the product. MS(ESI) m/z 386.4 (M+H)+.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was then purified by SiO2 chromatography (eluting with EtOAc/Heptane system)

Sources & evidence

ORD record
ord-ac6131e7882d47a8b1c12508684965f5
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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