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

HRID 1977763Notes

Reaction equation

HRID 1977763 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 (Na4SO4) 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 (Na4SO4)
  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-86a1684a94d54f658e158f0ece148b40
Source dataset
uspto-grants-2001_05
Patent number
US06235758B1

Reaction notes

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