Dimethylformamide → N-phenyl-4-dimethylamino-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide

HRID 1250486Notes

Reaction equation

HRID 1250486 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].Br[C:15]1[CH:20]=[C:19]([N:21]([CH3:23])[CH3:22])[CH:18]=[C:17](Br)[N:16]=1.[CH3:25][N:26]([CH:28]=[O:29])C>CCCCCC>[C:25]1([NH:26][C:28]([C:15]2[CH:20]=[C:19]([N:21]([CH3:23])[CH3:22])[CH:18]=[C:17]([O:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=3)[N:16]=2)=[O:29])[CH:5]=[CH:4][CH:3]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 73763-(Trifluoromethyl)phenolHCID 24758Sodium hydrideHCID 183262052,6-Dibromo-N,N-dimethylpyridin-4-amine

Product 1

HCID 15906597N-phenyl-4-dimethylamino-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

1.4 g (0.0071×1.2 mol) of 3-(trifluoromethyl) phenol was dissolved in about 20 ml of DMF. The solution was further mixed with 0.30 g (ca. 60% in mineral oil; 0.0071-1.06 mol) of NaH and then with 2.00 g (0.0071 mol) of 2,6-dibromo-4-dimethylamino pyridine. After treating the solution under reflux for about 6 hours, the resultant solution was allowed to stand for cooling to room temperature. After the reaction solution was distributed in hexane-saturated sodium bicarbonate water, the organic phase of the obtained solution was washed with saturated brine and dried with anhydrous sodium sulfate, followed by concentration thereof. Thereafter, the concentrated solution was purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane) and the obtained eluate was subjected to recrystallization using hexane, thereby obtaining an aimed product.

Workup

  1. additionAfter treating the solution
  2. temperatureunder reflux for about 6 hours
  3. washthe organic phase of the obtained solution was washed with saturated brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationfollowed by concentration
  6. customThereafter, the concentrated solution was purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)
  7. customthe obtained eluate was subjected to recrystallization

Sources & evidence

ORD record
ord-86094f1642164a0bb70efc9566863c2d
Source dataset
uspto-grants-2002_01
Patent number
US06339045B1

Reaction notes

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