Cesium carbonate → HCID 67185282, compound

HRID 1843660Notes

Reaction equation

HRID 1843660 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:14]([C:15](=[O:17])[CH3:16])=[CH:13][NH:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Cl)=[CH:28][CH:27]=1>CN(C)C=O>[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][N:12]2[CH:13]=[C:14]([C:15](=[O:17])[CH3:16])[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)=[N:11]2)=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 178467227HCID 178467227, compound

Product 1

HCID 67185282HCID 67185282, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

320 mg (1.39 mmol) of 1-[3-(3-nitrophenyl)-1H-pyrazol-4-yl]ethanone were dissolved with 15 ml of dry dimethylformamide and 540 mg (1.66 mmol) of cesium carbonate and 189 μl (1.39 mmol) of p-methoxybenzyl chloride were added. The reaction mixture was maintained at 70° C. under stirring for 8 hours. The solvent was then removed under reduced pressure and the residue taken up with dichloromethane and washed with water. The organic layer was dried over sodium sulphate and evaporated. The crude was finally purified by flash-chromatography on a silica gel column (cyclohexane-ethylacetate; from 4/1 to 3/2), giving 470 mg (97%) of the title compound.

Workup

  1. additionwere added
  2. customThe solvent was then removed under reduced pressure
  3. washwashed with water
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. customevaporated
  6. customThe crude was finally purified by flash-chromatography on a silica gel column (cyclohexane-ethylacetate; from 4/1 to 3/2)

Sources & evidence

ORD record
ord-b4664c7c9f614dbc98f25529d4da53c4
Source dataset
uspto-grants-2015_02
Patent number
US08946250B2

Reaction notes

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