Sodium hydride → cyclopropyl(4-(1,3-oxazol-5-yl)-6-(trifluoromethyl)-1H-indol-1-yl)methanone

HRID 931006Notes

Reaction equation

HRID 931006 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[C:5]([C:12]2[O:16][CH:15]=[N:14][CH:13]=2)[CH:4]=1.[H-].[Na+].[CH:21]1([C:24](Cl)=[O:25])[CH2:23][CH2:22]1.[Cl-].[NH4+]>CN(C=O)C>[CH:21]1([C:24]([N:9]2[C:10]3[C:6](=[C:5]([C:12]4[O:16][CH:15]=[N:14][CH:13]=4)[CH:4]=[C:3]([C:2]([F:17])([F:1])[F:18])[CH:11]=3)[CH:7]=[CH:8]2)=[O:25])[CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 77637Cyclopropanecarbonyl chlorideHCID 1183789305-(6-(trifluoromethyl)-1H-indol-4-yl)oxazole

Product 1

HCID 118378951cyclopropyl(4-(1,3-oxazol-5-yl)-6-(trifluoromethyl)-1H-indol-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(6-(trifluoromethyl)-1H-indol-4-yl)oxazole (50.0 mg) in DMF (1 mL) was added 60% sodium hydride (9.52 mg) at 0° C., and the mixture was stirred for 20 min. To the reaction mixture was added cyclopropanecarbonyl chloride (22 μL) at 0° C., and the mixture was stirred for 3 hr, saturated aqueous ammonium chloride solution was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), and the obtained solid was recrystallized from ethyl acetate/hexane to give the title compound (30.0 mg).

Workup

  1. stirringthe mixture was stirred for 3 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  7. customthe obtained solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-451270afcd5b44ba9b87c65f7f0dfbee
Source dataset
uspto-grants-2016_03
Patent number
US09296746B2

Reaction notes

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