Methyl iodide → HCID 15979551, compound

HRID 656505Notes

Reaction equation

HRID 656505 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[C:4]2([CH2:17][CH2:16][CH2:15][N:14]3[CH:18]=[N:19][CH:20]=[C:13]23)[NH:3]1.[H-].[Na+].[CH3:23]I>CN(C)C=O.O>[CH3:23][N:3]1[C:2](=[O:1])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[C:4]21[CH2:17][CH2:16][CH2:15][N:14]1[CH:18]=[N:19][CH:20]=[C:13]21

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15979550HCID 15979550, compound

Product 1

HCID 15979551HCID 15979551, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1 mmol of 3′-oxo-2′,3′,6,7-tetrahydro-5H-spiro[imidazo[1,5-a]pyridine-8,1′-isoindole]-5′-carbonitrile (Example 13) in 5 ml of N,N-dimethylformamide is treated with 1.2 mmol of sodium hydride (60% dispersion in oil). The reaction mixture is stirred for 20 minutes at room temperature, and then 1.2 mmol of methyl iodide are added. The reaction mixture is stirred for 20 minutes at room temperature, then diluted with water and extracted with tert-butyl methyl ether (3×). The combined organic phases are dried with sodium sulphate and evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60F) on the basis of the Rf value.

Workup

  1. stirringThe reaction mixture is stirred for 20 minutes at room temperature
  2. extractionextracted with tert-butyl methyl ether (3×)
  3. dry with materialThe combined organic phases are dried with sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-ab9948907a064f479e237ef24f72414a
Source dataset
uspto-grants-2011_12
Patent number
US08071774B2

Reaction notes

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