Methyl iodide → 1-methyl-1'-[6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridazin-3-yl]spiro[indole-3,3'-pyrrolidin]-2(1H)-one

HRID 2036119Notes

Reaction equation

HRID 2036119 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[N:12]=[N:11][C:10]([N:13]3[CH2:17][CH2:16][C:15]4([C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[NH:19][C:18]4=[O:26])[CH2:14]3)=[CH:9][CH:8]=2)[O:4][N:3]=1.[H-].[Na+].I[CH3:30]>CN(C)C=O>[CH3:30][N:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]2([CH2:16][CH2:17][N:13]([C:10]3[N:11]=[N:12][C:7]([C:5]4[O:4][N:3]=[C:2]([CH3:1])[N:6]=4)=[CH:8][CH:9]=3)[CH2:14]2)[C:18]1=[O:26]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 685546001'-[6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridazin-3-yl]spiro[indole-3,3'-pyrrolidin]-2(1H)-one

Product 1

HCID 250010001-methyl-1'-[6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridazin-3-yl]spiro[indole-3,3'-pyrrolidin]-2(1H)-oneYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1′-[6-(3-Methyl-1,2,4-oxadiazol-5-yl)pyridazin-3-yl]spiro[indole-3,3′-pyrrolidin]-2(1H)-one (300 mg) obtained in Example 158 was dissolved in N,N-dimethylformamide (10 mL), sodium hydride (60 w %, 35 mg) was added, and the mixture was stirred at room temperature for 30 min. Iodomethane (0.054 mL) was added, and the mixture was further stirred at room temperature for 3 hr. The reaction was quenched with saturated aqueous ammonium chloride solution, and water (20 mL) was added. The resulting precipitate was collected by filtration to give the object product (198 mg, 64%).

Workup

  1. stirringthe mixture was further stirred at room temperature for 3 hr
  2. customThe reaction was quenched with saturated aqueous ammonium chloride solution, and water (20 mL)
  3. additionwas added
  4. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-96d7a5782c9d490ebbbd1d2574924b0f
Source dataset
uspto-grants-2013_11
Patent number
US08575167B2

Reaction notes

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