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Ethyl Acetate → HCID 22000062, compound

HRID 1975948
Notes
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Reaction equation

HRID 1975948 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15].C[Si](C)(C)[N-][Si](C)(C)C.[K+].[F:26][C:27]([F:45])([F:44])[C:28]1[CH:29]=[C:30]([C:38]([CH3:43])([CH3:42])[C:39](Cl)=[O:40])[CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1.C(OCC)(=O)C>CN(C)C=O.O1CCCC1>[F:26][C:27]([F:45])([F:44])[C:28]1[CH:29]=[C:30]([C:38]([CH3:43])([CH3:42])[C:39]([N:2]([CH3:1])[C:3]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[O:40])[CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 112671412-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chlorideHCID 22000072HCID 22000072, compound

Product 1

HCID 22000062HCID 22000062, compoundYield 61.9%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 140 mg (0.71 mmol) methyl-(3-o-tolyl-pyridin-4-yl)-amine in 1 ml N,N-dimethylformamide at 0° C. were added dropwise 0.71 ml (0.71 mmol) of 1 M potassium hexamethyldisilazide solution in tetrahydrofuran. Stirring was continued for 1 h at room temperature and the reaction mixture was cooled to 0° C. again. At this temperature, a solution of 270 mg (0.85 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride in 0.5 ml tetrahydrofuran was added. After stirring for 18 h at room temperature, ethyl acetate was added and the organic phase was washed with brine, dried (magnesium sulfate) and evaporated. The residue was purified by flash chromatography to give 211 mg (58%) of the title compound as white foam.

Workup

  1. stirringAfter stirring for 18 h at room temperature
  2. washthe organic phase was washed with brine
  3. dry with materialdried (magnesium sulfate)
  4. customevaporated
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-8c28b74508b24bbe87e9a45654736211
Source dataset
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06225316B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes