Sodium hydride → HCID 58495462, compound

HRID 1191097Notes

Reaction equation

HRID 1191097 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[N:4]1.Br[CH2:17][CH:18]1[CH2:20][CH2:19]1>CN(C=O)C>[CH:18]1([CH2:17][N:3]2[CH:7]=[CH:6][C:5]([C:8]3[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=3)=[N:4]2)[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 178509584HCID 178509584, compound

Product 1

HCID 58495462HCID 58495462, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Add sodium hydride (64 mg, 2.65 mmol) to a solution of 4-(1H-pyrazol-3-yl)-benzonitrile (300 mg, 1.77 mmol) in DMF (5 mL) under nitrogen atmosphere. Stir the mixture for 15 min at 0° C. and add (bromomethyl)cyclopropane (206 □l, 2.12 mmol). Stir the mixture for 5 min at 0° C. and then at room temperature overnight. Quenck the reaction mixture with water and extract twice with EtOAc. Dry the combined organics extracts over Na2SO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (75:25) to obtain the desired intermediate (256 mg, 65%).

Workup

  1. stirringStir the mixture for 5 min at 0° C.
  2. customat room temperature
  3. customovernight
  4. extractionQuenck the reaction mixture with water and extract twice with EtOAc
  5. customDry the combined
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (75:25)

Sources & evidence

ORD record
ord-84cf1d1f9e7140e2bb937f216d417bbb
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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