Cesium carbonate → 1-(4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1364210Notes

Reaction equation

HRID 1364210 reaction equation
I[C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][C@H:11]2[CH3:15])=[CH:4][CH:3]=1.[CH2:18]([O:20][C:21]([C:23]1[CH:24]=[N:25][NH:26][CH:27]=1)=[O:22])[CH3:19].CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O.[Cu](I)I>[CH2:18]([O:20][C:21]([C:23]1[CH:24]=[N:25][N:26]([C:2]2[CH:17]=[CH:16][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]3[CH2:14][CH2:13][CH2:12][C@H:11]3[CH3:15])=[CH:4][CH:3]=2)[CH:27]=1)=[O:22])[CH3:19]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 57675747(2R)-1-[3-(4-iodophenoxy)propyl]-2-methylpyrrolidine

Product 1

HCID 595417211-(4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of (2R)-1-[3-(4-iodophenoxy)propyl]-2-methylpyrrolidine obtained in Example 1-(2) (1.60 g), 1H-pyrazole-4-carboxylic acid ethyl ester (0.779 g), (rac-trans-N,N′-dimethylcyclohexane-1,2-diamine (0.263 g), copper iodide (0.088 g) and cesium carbonate (3.02 g) in N,N-dimethylformamide (2.5 mL) was stirred at 120° C. for 4 hours. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=3:1) to give the titled compound (1.11 g) as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-abe40779c6b943c4bd6ee96249ea942c
Source dataset
uspto-grants-2011_02
Patent number
US07888354B2

Reaction notes

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