Cesium carbonate → 2-{[5-amino-4-(1,3-benzodioxol-5-yl)-1-benzyl-1H-pyrazol-3-yl]oxy}ethyl Acetate

HRID 1062808Notes

Reaction equation

HRID 1062808 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([OH:14])[C:3]=1[C:15]1[CH:23]=[CH:22][C:18]2[O:19][CH2:20][O:21][C:17]=2[CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:30]([O:33][CH2:34][CH2:35]Br)(=[O:32])[CH3:31]>CN(C)C=O>[C:30]([O:33][CH2:34][CH2:35][O:14][C:4]1[C:3]([C:15]2[CH:23]=[CH:22][C:18]3[O:19][CH2:20][O:21][C:17]=3[CH:16]=2)=[C:2]([NH2:1])[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=1)(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 135641-Acetoxy-2-bromoethaneHCID 178507199HCID 178507199, compound

Product 1

HCID 222819442-{[5-amino-4-(1,3-benzodioxol-5-yl)-1-benzyl-1H-pyrazol-3-yl]oxy}ethyl AcetateYield 58.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 5-amino-4-(1,3-benzodioxol-5-yl)-1-benzyl-1H-pyrazol-3-ol (30 g) (Preparation 59) and cesium carbonate (94.8 g) in anhydrous dimethylformamide (340 ml), under an atmosphere of nitrogen, 2-bromoethyl acetate (16.2 g) was added drop-wise over 10 minutes and the reaction was stirred overnight. The reaction was quenched by the addition of an aqueous solution of HCl (2N, 260 ml) then ethyl acetate (600 ml) and water (1000 ml) were added. The aqueous phase was extracted with ethyl acetate (3×500 ml) and the combined organic fractions were washed with brine (500 ml) and dried over Na2SO4. The dark oil was purified by flash chromatography (heptane/EtOAc; 1/1) (silica, 1000 g) yielding of the title compound as a dark oil (22.5 g).

Workup

  1. customThe reaction was quenched by the addition of an aqueous solution of HCl (2N, 260 ml)
  2. additionethyl acetate (600 ml) and water (1000 ml) were added
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×500 ml)
  4. washthe combined organic fractions were washed with brine (500 ml)
  5. dry with materialdried over Na2SO4
  6. customThe dark oil was purified by flash chromatography (heptane/EtOAc; 1/1) (silica, 1000 g)

Sources & evidence

ORD record
ord-3819f4bfe7254b7a9bb96c86928934bf
Source dataset
uspto-grants-2005_11
Patent number
US06962923B2

Reaction notes

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