3-(Trifluoromethyl)phenol → HCID 15906604, compound

HRID 1250492Notes

Reaction equation

HRID 1250492 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+].[CH2:14]([NH:21][C:22]([C:24]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26](Br)[N:25]=1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C.C(OCC)(=O)C.[Cu](Cl)Cl>[CH2:14]([NH:21][C:22]([C:24]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26]([O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=2)[N:25]=1)=[O:23])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 24758Sodium hydrideHCID 18326222HCID 18326222, compound

Product 1

HCID 15906604HCID 15906604, compound

Reagents, catalysts & solvents 3

HCID 24014Cupric ChlorideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

1.04 g (0.0029×2.2 mol) of 3-(trifluoromethyl) phenol was dissolved in about 10 ml of DMF. The obtained solution was further mixed with 0.24 g (ca. 60% in mineral oil; 0.0029×2.0 mol) of NaH and then with 0.94 g (0.0029 mol) of N-benzyl-6-bromo-4-methoxy-2-pyridine carboxamide. After adding 0.15 g (0.0029×0.5 mol) of copper chloride (I), the solution was stirred at about 120° C. for about 5 hours, and then allowed to stand for cooling to room temperature. After the reaction solution was distributed in ethyl acetate-saturated sodium bicarbonate water, the organic phase of the 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), thereby obtaining an aimed product.

Workup

  1. temperaturefor cooling to room temperature
  2. washthe organic phase of the solution was washed with saturated brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationfollowed by concentration
  5. customThereafter, the concentrated solution was purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-96976284f202477cbcea5228ce346bed
Source dataset
uspto-grants-2002_01
Patent number
US06339045B1

Reaction notes

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