Water → (6-Bromo-quinoxalin-2-yl)-(4-fluoro-3-trifluoromethyl-benzyl)-methyl-amine

HRID 1020740Notes

Reaction equation

HRID 1020740 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([NH:14][CH3:15])[CH:8]=[N:7]2.Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[C:20]([C:25]([F:28])([F:27])[F:26])[CH:19]=1.O>CN(C=O)C>[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([N:14]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[C:20]([C:25]([F:28])([F:26])[F:27])[CH:19]=1)[CH3:15])[CH:8]=[N:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27375774-Fluoro-3-(trifluoromethyl)benzyl bromideHCID 601459936-Bromo-N-methylquinoxalin-2-amine

Product 1

HCID 66797280(6-Bromo-quinoxalin-2-yl)-(4-fluoro-3-trifluoromethyl-benzyl)-methyl-amineYield 67.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (0.08 g, 1.5 eq, 3.37 mmol) in DMF (15 mL) was added (6-Bromo-quinoxalin-2-yl)-methyl-amine (0.6 g, 1.0 eq, 2.51 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 15 minutes. A mixture of 4-(bromomethyl)-1-fluoro-2-(trifluoromethyl)benzene (0.7 g, 1.2 eq. 2.72 mmol) in DMF (15 mL) was added at room temperature and the reaction mixture was stirred for 2.0 hours at 0° C. After completion of the reaction, cold water (180 mL) was added and the reaction mixture was stirred for 15 minutes then filtered. The solid was dried under vacuum to afford the title compound (0.7 g, 67%).

Workup

  1. additionwas added at room temperature
  2. stirringthe reaction mixture was stirred for 2.0 hours at 0° C
  3. additionwas added
  4. stirringthe reaction mixture was stirred for 15 minutes
  5. filtrationthen filtered
  6. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-615a267c0def440eb228d4cac085e15e
Source dataset
uspto-grants-2014_05
Patent number
US08716473B2

Reaction notes

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