Cesium carbonate → HCID 69380447, compound

HRID 1296940Notes

Reaction equation

HRID 1296940 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][NH:12][C:13]=2[CH3:14])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:21][Si:22]([CH3:29])([CH3:28])[CH2:23][CH2:24][O:25][CH2:26]Cl>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[N:11][N:12]([CH2:26][O:25][CH2:24][CH2:23][Si:22]([CH3:29])([CH3:28])[CH3:21])[C:13]=2[CH3:14])=[CH:7][CH:8]=1.[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:13]([CH3:14])=[N:12][N:11]([CH2:26][O:25][CH2:24][CH2:23][Si:22]([CH3:29])([CH3:28])[CH3:21])[CH:10]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 2805464HCID 2805464, compound

Product 2

HCID 69380447HCID 69380447, compoundHCID 69380517HCID 69380517, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-(4-Methoxy-phenyl)-5-methyl-1H-pyrazole (1 eq) was taken up in DMF and under N2 was cooled to 0° C. Caesium carbonate (1 eq) was added and the solution was stirred for five minutes. 2-(Trimethylsilyl)ethoxy methyl chloride (0.95 eq) was added dropwise and all was stirred for 2 hours. The reaction mixture was partitioned between water and EtOAc. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give a gum. This was purified by flash chromatography (8:1 hexane: EtOAc) to give 4-(4-methoxy-phenyl)-5-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazole and 4-(4-methoxy-phenyl)-3-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazole as a mixture of isomers.

Workup

  1. stirringall was stirred for 2 hours
  2. customThe reaction mixture was partitioned between water and EtOAc
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a gum
  7. customThis was purified by flash chromatography (8:1 hexane: EtOAc)

Sources & evidence

ORD record
ord-9351743a771649adbf6d237e16ec0323
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

Loading…