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Methyl iodide → 2-(4-((6-Fluoro-2-quinoxalinyl)oxy)phenoxy)-N-methyl-N-(4-(trifluoromethoxy)phenyl)propanamide

HRID 1655546
Notes
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Reaction equation

HRID 1655546 reaction equation
[H-].[Na+].[CH3:3]CCCCC.[F:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([O:20][C:21]1[CH:43]=[CH:42][C:24]([O:25][CH:26]([CH3:41])[C:27]([NH:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=3)=[O:28])=[CH:23][CH:22]=1)[CH:14]=[N:13]2.CI>CN(C=O)C>[F:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([O:20][C:21]1[CH:43]=[CH:42][C:24]([O:25][CH:26]([CH3:41])[C:27]([N:29]([CH3:3])[C:30]3[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=3)=[O:28])=[CH:23][CH:22]=1)[CH:14]=[N:13]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8058HexaneHCID 24758Sodium hydrideHCID 197926992-(4-((6-Fluoro-2-quinoxalinyl)oxy)phenoxy)-N-(4-(trifluoromethoxy)phenyl)propanamide

Product 1

HCID 197926882-(4-((6-Fluoro-2-quinoxalinyl)oxy)phenoxy)-N-methyl-N-(4-(trifluoromethoxy)phenyl)propanamideYield 50%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 0.23 g (5.7 mmol) of a 60 percent NaH/oil dispersion and 10 ml of hexane was stirred under N2 for 10 minutes. The hexane was decanted off, replaced with 20 ml of DMF and a solution of 2.0 g (4.1 mmol) of 2-(4-((6-fluoro-2-quinoxalinyl)oxy)phenoxy)-N-(4-(trifluoromethoxy)phenyl)propanamide in 20 ml of DMF was added dropwise over a period of 30 minutes. The mixture was stirred at ambient temperature for 1.5 hours when a solution of 1.45 g (10 mmol) of methyl iodide in 10 ml of DMF was slowly added. The mixture was stirred at ambient temperature for 2 days and then quenched by cautious addition of a few drops of acetic acid and then water. The mixture was poured into water, extracted with three portions of ether and the combined organic layers dried over MgSO4 and evaporated to dryness. The residue was taken up in hot methylcyclohexane, treated with charcoal and filtered and then allowed to cool to give 1.03 g (50 percent) of the above-named product as colorless crystals, m.p. 137°-139° C. (Compound 41)

Workup

  1. customThe hexane was decanted off
  2. additionwas slowly added
  3. stirringThe mixture was stirred at ambient temperature for 2 days
  4. customquenched by cautious addition of a few drops of acetic acid
  5. additionThe mixture was poured into water
  6. extractionextracted with three portions of ether
  7. dry with materialthe combined organic layers dried over MgSO4
  8. customevaporated to dryness
  9. additiontreated with charcoal
  10. filtrationfiltered
  11. temperatureto cool

Sources & evidence

ORD record
ord-6b5a2750aadb427d9df82f205917f3d5
Source dataset
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05250690

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes