Sodium hydride → HCID 117798685, compound

HRID 1497360Notes

Reaction equation

HRID 1497360 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[CH3:13].[CH2:14](I)[CH2:15][CH3:16].[Cl-].[NH4+]>CN(C)C=O>[Br:3][C:4]1[CH:12]=[CH:11][C:10]2[C:6](=[C:7]([CH3:13])[N:8]([CH2:14][CH2:15][CH3:16])[N:9]=2)[CH:5]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 336431-IodopropaneHCID 178434225HCID 178434225, compound

Product 1

HCID 117798685HCID 117798685, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 60% sodium hydride (85 mg) in N,N-dimethylformamide (10 ml) was added a solution of 5-bromo-3-methyl-1H-indazole (500 mg) in N,N-dimethylformamide (1 ml) at 0° C., and the mixture was stirred at the same temperature for 30 min. To the obtained reaction mixture was added propyl iodide (0.35 ml), and the mixture was stirred at room temperature for 3 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (100 mg).

Workup

  1. customTo the obtained reaction mixture
  2. stirringthe mixture was stirred at room temperature for 3 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b39684b2090e4e328218cd56c9a437b6
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

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