3-Bromopentane → HCID 58938696, compound

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

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.