5-Methoxy-6-(trifluoromethyl)indoline → HCID 10837468, compound

HRID 1977775Notes

Reaction equation

HRID 1977775 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:15]3[O:14][CH2:13][CH2:12][C:11]=3[CH:10]=[C:9]([NH:16][C:17](=[O:25])OC3C=CC=CC=3)[CH:8]=2)[CH:2]=1.[CH3:26][O:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][C:36]=1[C:37]([F:40])([F:39])[F:38])[NH:33][CH2:32][CH2:31]2>CN(C=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:15]3[O:14][CH2:13][CH2:12][C:11]=3[CH:10]=[C:9]([NH:16][C:17]([N:33]3[C:34]4[C:30](=[CH:29][C:28]([O:27][CH3:26])=[C:36]([C:37]([F:39])([F:40])[F:38])[CH:35]=4)[CH2:31][CH2:32]3)=[O:25])[CH:8]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 112067135-Methoxy-6-(trifluoromethyl)indolineHCID 18005145HCID 18005145, compound

Product 1

HCID 10837468HCID 10837468, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phenyl N-[2,3-dihydro-7-(pyrid-3-yl)benzofuran-5-yl]carbamate (D65) (0.20 g, 0.00060 mole) in dry DMF (10 ml) was treated under argon with 5-methoxy-6-trifluoromethyl indoline (D11) (0.13 g, 0.00060 mole) and heated under reflux for 18 hours. The reaction was allowed to cool to ambient temperature and the solvent was removed in vacuo. The residue was dissolved in dichloromethane, washed with deionised water and 10% sodium hydroxide solution, dried (Na2SO4) and evaporated in vacuo. The resulting brown oil was purified by flash column chromatography on silica gel, eluting with 2% methanol/dichloromethane, followed by recrystallisation from ethyl acetate 60-80° petroleum ether to afford the title compound (0.07 g, 26%) as a beige solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 18 hours
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with deionised water and 10% sodium hydroxide solution
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe resulting brown oil was purified by flash column chromatography on silica gel
  9. washeluting with 2% methanol/dichloromethane
  10. customfollowed by recrystallisation from ethyl acetate 60-80° petroleum ether

Sources & evidence

ORD record
ord-2b31aaa675484999baca45fd52d7b539
Source dataset
uspto-grants-2001_05
Patent number
US06235758B1

Reaction notes

Loading…