Cesium carbonate → HCID 22281967, compound

HRID 1368647Notes

Reaction equation

HRID 1368647 reaction equation
[NH2:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)=[C:5]([OH:14])[N:4]([CH3:15])[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:22]([O:25][CH2:26][CH2:27]Br)(=[O:24])[CH3:23]>CN(C)C=O.Cl>[C:22]([O:25][CH2:26][CH2:27][O:14][C:5]1[N:4]([CH3:15])[N:3]=[C:2]([NH2:1])[C:6]=1[C:7]1[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][CH:12]=1)(=[O:24])[CH3:23]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 135641-Acetoxy-2-bromoethaneHCID 178423894HCID 178423894, compound

Product 1

HCID 22281967HCID 22281967, compoundYield 12.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To 3-amino-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-ol (Preparation 3b) (855 mg) in dimethylformamide (10 ml) at room temperature was added cesium carbonate (4.11 g) and 2-bromoethyl acetate (703 mg), the mixture was stirred for 45 minutes. The reaction was diluted with 2M hydrochloric acid (10 ml) and extracted with ether (2×100 ml). The organic fractions were combined, washed with water (2×100 ml) and brine (100 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica, 30 g) eluted with ethyl acetate:hexane (5:1) to yield the title compound as a white solid (155 mg).

Workup

  1. extractionextracted with ether (2×100 ml)
  2. washwashed with water (2×100 ml) and brine (100 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica, 30 g)
  7. washeluted with ethyl acetate:hexane (5:1)

Sources & evidence

ORD record
ord-9c2e68ccb81f45d6a6be90310a619d54
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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