3-Bromopentane → HCID 58938696, compound

HRID 598090Notes

Reaction equation

HRID 598090 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11](=[O:19])[N:12]([CH3:18])[NH:13]2.[H-].[Na+].Br[CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25]>CN(C)C=O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11](=[O:19])[N:12]([CH3:18])[N:13]2[CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 157383-BromopentaneHCID 24758Sodium hydrideHCID 67267316HCID 67267316, compound

Product 1

HCID 58938696HCID 58938696, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution containing 0.008 g (0.03 mmol) of 4-(2,4-dimethylphenyl)-2-methyl-1,2-dihydro-3H-indazol-3-one in 2 ml of N,N-dimethylformamide under a nitrogen atmosphere was added 0.001 g (0.038 mmol) of sodium hydride followed by 0.007 g (0.048 mmol) of 3-bromopentane. The reaction was allowed to stir at room temperature for 48 h, quenched with water and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via biotage eluting with 25% ethyl acetate/dichloromethane gave 0.003 g (30%) of compound.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationFiltration, removal of solvent and purification of the residue via biotage
  5. washeluting with 25% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-d4758c9e8f06425fb446e64c0fb66484
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

Loading…