Methyl iodide → HCID 44251386, compound

HRID 2189473Notes

Reaction equation

HRID 2189473 reaction equation
C(O[C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17](=[O:34])[N:18]([CH3:33])[C:19]2[CH:20]=[N:21][C:22]([O:25][C:26]3[C:27]([CH3:32])=[N:28][CH:29]=[CH:30][CH:31]=3)=[CH:23][CH:24]=2)=[CH:9]1)=O)(C)(C)C.[H-].[Na+].CI>C1COCC1>[CH3:33][N:18]([C:19]1[CH:20]=[N:21][C:22]([O:25][C:26]2[C:27]([CH3:32])=[N:28][CH:29]=[CH:30][CH:31]=2)=[CH:23][CH:24]=1)[C:17]([C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]([CH3:6])[CH:9]=1)=[O:34]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68968247HCID 68968247, compound

Product 1

HCID 44251386HCID 44251386, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The tert-butyl-3-(methyl(6-(2-methylpyridine-3-yloxy)pyridine-3-yl)carbamoyl)-1H-indole-1-carboxylate (40 mg, 0.087 mmol) in Example 12 was dissolved in THF (10 ml), and NaH (21 mg, 0.54 mmol) and methyl iodide (0.95 g, 0.67 mmol) were added to the solution. The reaction solution was stirred at room temperature for 5 hours, and then the product was washed and filtered to yield a target compound as a brown solid (20 mg, 12%) by chromatography (methanol:dichloromethane=1:20).

Workup

  1. washthe product was washed
  2. filtrationfiltered

Sources & evidence

ORD record
ord-8a849f6d51c34baeb4b2ebccae9640c3
Source dataset
uspto-grants-2012_12
Patent number
US08324246B2

Reaction notes

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