Acetonitrile → 6-(5-Bromo-2-fluorophenyl)-N-(2-(2-fluorophenyl)propan-2-yl)-1,2,4-triazin-3-amine

HRID 2276770Notes

Reaction equation

HRID 2276770 reaction equation
Br[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][C:9]=2[F:15])=[CH:6][N:7]=1.[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]([NH2:26])([CH3:25])[CH3:24].C([O-])([O-])=O.[K+].[K+].CC#N>CCOC(C)=O>[Br:14][C:12]1[CH:11]=[CH:10][C:9]([F:15])=[C:8]([C:5]2[N:4]=[N:3][C:2]([NH:26][C:23]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[F:16])([CH3:25])[CH3:24])=[N:7][CH:6]=2)[CH:13]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 135695202-(2-Fluorophenyl)propan-2-amineHCID 866868233-Bromo-6-(5-bromo-2-fluorophenyl)-1,2,4-triazine

Product 1

HCID 866868246-(5-Bromo-2-fluorophenyl)-N-(2-(2-fluorophenyl)propan-2-yl)-1,2,4-triazin-3-amineYield 67.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Bromo-6-(5-bromo-2-fluorophenyl)-1,2,4-triazine (2.8 g, 8.4 mmol), 2-(2-fluorophenyl)propan-2-amine (2.0 g, 12.6 mmol), K2CO3 (2.3 g, 16.8 mmol) and CH3CN (20 mL) was heated to 90° C. The reaction mixture was diluted with EtOAc and washed with satd. aq. NaHCO3 and brine. The organic layer was dried over sodium sulfate, filtered, concentrated, and purified using silica gel chromatography to afford a yellow solid (2.3 g), m/z=406.1 [M+H].

Workup

  1. washwashed with satd
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified

Sources & evidence

ORD record
ord-b3bb45e774414efeb5124266787b9838
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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