Methanol → HCID 68968247, compound

HRID 2189471Notes

Reaction equation

HRID 2189471 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17](=[O:33])[NH:18][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:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:36]I.CO>C1COCC1.ClCCl>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17](=[O:33])[N:18]([CH3:36])[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:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68967991HCID 68967991, compound

Product 1

HCID 68968247HCID 68968247, compoundYield 16.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The 1H-indole-3-carboxylic acid[6-(2-methyl-pyridine-3-yloxy)-pyridine-3-yl]-amide (0.2 g, 0.58 mmol) in Example 6 was dissolved in dichloromethane (10 ml), and Boc2O (0.15 g, 0.7 mmol) and triethylamine (0.12 g, 1.16 mmol) were added to the solution. The reaction solution was stirred at room temperature for 2 hours, and then the product was washed, filtered, and dried to obtain tert-butyl-3-(6-(2-methylpyridine-3-yloxy)pyridine-3-ylcarbamoyl)-1H-indole-1-carboxylate (0.27 g, 0.52 mmol). The tert-butyl-3-(6-(2-methylpyridine-3-yloxy)pyridine-3-ylcarbamoyl)-1H-indole-1-carboxylate (0.27 g, 0.52 mmol) 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 tert-butyl-3-(methyl(6-(2-methylpyridine-3-yloxy)pyridine-3-yl)carbamoyl)-1H-indole-1-carboxylate (40 mg, 0.087 mmol) by chromatography (methanol:dichloromethane=1:20).

Workup

  1. washthe product was washed
  2. filtrationfiltered

Sources & evidence

ORD record
ord-358aaf72a8c249b6a95dc1ff44380e1a
Source dataset
uspto-grants-2012_12
Patent number
US08324246B2

Reaction notes

Loading…