Sodium hydride → 1-[(5-bromo-3-methyl-2H-indazol-2-yl)methyl]cyclopropanecarbonitrile

HRID 1497363Notes

Reaction equation

HRID 1497363 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].CC1C=CC(S(O[CH2:25][C:26]2([C:29]#[N:30])[CH2:28][CH2:27]2)(=O)=O)=CC=1.[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]([CH2:25][C:26]3([C:29]#[N:30])[CH2:28][CH2:27]3)[N:9]=2)[CH:5]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22028201(1-Cyanocyclopropyl)methyl 4-methylbenzenesulfonateHCID 178434225HCID 178434225, compound

Product 1

HCID 1177986131-[(5-bromo-3-methyl-2H-indazol-2-yl)methyl]cyclopropanecarbonitrileYield 12.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 60% sodium hydride (143 mg) in N,N-dimethylformamide (3 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 (1-cyanocyclopropyl)methyl 4-methylbenzenesulfonate (420 mg), and the mixture was stirred at room temperature for 16 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with dichloromethane. 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 (60 mg).

Workup

  1. customTo the obtained reaction mixture
  2. stirringthe mixture was stirred at room temperature for 16 hr
  3. extractionthe mixture was extracted with dichloromethane
  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-28d74b7291524c9aaa15b46ccdbdca5f
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

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