Potassium Carbonate → {5-Methyl-2-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]-2H-pyrazol-3-yl}methanol

HRID 1013039Notes

Reaction equation

HRID 1013039 reaction equation
[OH:1][CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[N:6]=[C:5]([CH3:15])[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:23][CH2:24][CH2:25][N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>CC(=O)CC.O>[CH3:15][C:5]1[CH:4]=[C:3]([CH2:2][OH:1])[N:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:23][CH2:24][CH2:25][N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:10][CH:9]=2)[N:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 113210281-(3-Chloropropyl)-pyrrolidineHCID 589487664-(5-Hydroxymethyl-3-methylpyrazol-1-yl)phenol

Product 1

HCID 24784814{5-Methyl-2-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]-2H-pyrazol-3-yl}methanolYield 62.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(5-hydroxymethyl-3-methylpyrazol-1-yl)phenol (326 mg, 1.60 mmol) in 2-butanone (8 mL) was added potassium carbonate (243 mg, 1.76 mmol) and 1-(3-chloropropyl)pyrrolidine (260 mg, 1.76 mmol). The reaction was heated overnight at 80° C. After the reaction was diluted with water and extracted with methylene chloride, the organic layer was dried (MgSO4) and concentrated to give 315 mg of the desired product. LC-MS (C18H25N3O2 calculated 315) m/z 316 (M+H).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialthe organic layer was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a177010a775a43f7ba6681966ef55d7d
Source dataset
uspto-grants-2011_07
Patent number
US07981896B2

Reaction notes

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