Potassium Carbonate → (4-((5-(4-(oxiran-2-ylmethoxy)phenyl)-1H-pyrazol-1-yl)methyl)phenyl)(pyrrolidin-1-yl)methanone

HRID 1399811Notes

Reaction equation

HRID 1399811 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([N:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)=[O:21])=[CH:16][CH:15]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Br[CH2:28][CH:29]1[CH2:31][O:30]1.C([O-])([O-])=O.[K+].[K+]>CC(=O)CC>[O:30]1[CH2:31][CH:29]1[CH2:28][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([N:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)=[O:21])=[CH:16][CH:15]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 136341374(4-((5-(4-hydroxyphenyl)-1H-pyrazol-1-yl)methyl)phenyl)(pyrrolidin-1-yl)methanone

Product 1

HCID 86729229(4-((5-(4-(oxiran-2-ylmethoxy)phenyl)-1H-pyrazol-1-yl)methyl)phenyl)(pyrrolidin-1-yl)methanoneYield 99.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

(4-((5-(4-hydroxyphenyl)-1H-pyrazol-1-yl)methyl)phenyl)(pyrrolidin-1-yl)methanone (173 mg, 0.5 mmol), 2-(bromomethyl)oxirane (544 mg, 3 mmol) and K2CO3 (552 mg, 4 mmol) were charged to a 100-mL flask containing 2-butanone (20 mL) and heated at reflux temperature for 17 h. The mixture was cooled, filtered and evaporated in vacuuo to give crude product as an oil (201 mg, 98%). This crude material was used without further purification. LCMS (m/z): 404.2 [M+H]

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 17 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. customevaporated in vacuuo

Sources & evidence

ORD record
ord-3209811264824d38a3966d1fcabab19a
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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