5-Methoxy-6-(trifluoromethyl)indoline → HCID 10623020, compound

HRID 989202Notes

Reaction equation

HRID 989202 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:17])OC2C=CC=CC=2)=[CH:4][C:3]=1[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[CH3:24].[CH3:25][O:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][C:35]=1[C:36]([F:39])([F:38])[F:37])[NH:32][CH2:31][CH2:30]2>CN(C)C=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:32]2[C:33]3[C:29](=[CH:28][C:27]([O:26][CH3:25])=[C:35]([C:36]([F:38])([F:39])[F:37])[CH:34]=3)[CH2:30][CH2:31]2)=[O:17])=[CH:4][C:3]=1[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[CH3:24]

Participants

4

Reactant 2

HCID 112067135-Methoxy-6-(trifluoromethyl)indolineHCID 18005125HCID 18005125, compound

Product 1

HCID 10623020HCID 10623020, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Phenyl N-(4-Methyl-3-(4-methylpyrid-3-yl)phenyl)carbamate (D69) (0.5 g, 0.0016 mole) in dry dimethylformamide (20 ml) was treated with 5-methoxy-6-trifluoromethylindoline (D11) (0.34 g, 0.0016 mole) under argon and heated to 100° C. for 6 hrs. The mixture was allowed to cool and evaporated to dryness in vacuo. The residue was dissolved in dichloromethane and the solution washed with 10% aqueous sodium hydroxide solution (2×20 ml) and then with saturated aqueous sodium chloride solution (30 ml). The organic phase was then dried (Na2SO4) filtered and evaporated to dryness. The residue was purified by flash chromatography on silica gel eluting with 1% methanol/dichloromethane. Trituration of the resulting residue with diethyl ether gave the title compound (E28) (0.326 g, 47%) m.p. 138-140° C.

Workup

  1. temperatureto cool
  2. customevaporated to dryness in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washthe solution washed with 10% aqueous sodium hydroxide solution (2×20 ml)
  5. dry with materialThe organic phase was then dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified by flash chromatography on silica gel eluting with 1% methanol/dichloromethane

Sources & evidence

ORD record
ord-68eb3a7ccb5d4669a6928046349b1082
Source dataset
uspto-grants-2003_10
Patent number
US06638953B2

Reaction notes

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