Water → HCID 86692517, compound

HRID 1748573Notes

Reaction equation

HRID 1748573 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][CH:8]1[CH2:13][CH2:12][C:11]([C:14]2[C:19]([CH3:20])=[CH:18][C:17]([Br:21])=[CH:16][N:15]=2)=[CH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:25]I.O>CN(C)C=O>[C:1]([O:5][C:6](=[O:22])[N:7]([CH:8]1[CH2:13][CH2:12][C:11]([C:14]2[C:19]([CH3:20])=[CH:18][C:17]([Br:21])=[CH:16][N:15]=2)=[CH:10][CH2:9]1)[CH3:25])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86692518HCID 86692518, compound

Product 1

HCID 86692517HCID 86692517, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[4-(5-bromo-3-methylpyridin-2-yl)cyclohex-3-en-1-yl]carbamic acid-tert-butyl ester (11.2 g) in N,N-dimethylformamide (90 ml) was added sodium hydride (1.46 g) under ice-cooling, and stirred at the same temperature for 0.5 hours. Then methyl iodide (5.7 ml) was added thereto, and stirred at the same temperature for 2 hours. After completion of the reaction, water was added thereto, and the precipitated solid was collected by filtration to give N-[4-(5-bromo-3-methylpyridin-2-yl)cyclohex-3-en-1-yl]-N-methylcarbamic acid-tert-butyl ester.

Workup

  1. temperaturecooling
  2. stirringstirred at the same temperature for 2 hours
  3. additionwas added
  4. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-9582345c10244b6e82ff9adccfb7f85d
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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