Pyrazole → HCID 56978789, compound

HRID 1430220Notes

Reaction equation

HRID 1430220 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.Br[CH2:7][CH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH:8]1([CH2:7][N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 1048PyrazoleHCID 14798Sodium HydroxideHCID 12723264(Bromomethyl)cyclopentane

Product 1

HCID 56978789HCID 56978789, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A flask was charged with pyrazole (380 mg), (bromomethyl)cyclopentane (968 mg), tetrabutylammonium bromide (18 mg), 50% aqueous NaOH (0.6 mL) and toluene (1.5 mL) and the mixture was heated to 110° C. for 4.5 hours. The reaction mixture was cooled to room temperature and partitioned between toluene (3×10 mL) and H2O (10 mL). The extracts were dried (MgSO4), filtered, and concentrated to give the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between toluene (3×10 mL) and H2O (10 mL)
  3. dry with materialThe extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0db9d783294744b8975ea872b964169d
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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