Indoline → HCID 12524226, compound

HRID 1725420Notes

Reaction equation

HRID 1725420 reaction equation
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.CN(C)[C:18](=[O:21])[CH:19]=[CH2:20].[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24]1>ClC(Cl)C>[CH2:25]1[C:26]2=[C:31]3[C:30](=[CH:29][CH:28]=[CH:27]2)[C:18](=[O:21])[CH2:19][CH2:20][N:23]3[CH2:24]1

Participants

5

Reactant 3

HCID 10328IndolineHCID 17587N,N-DimethylacrylamideHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 12524226HCID 12524226, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent3×

Procedure

Add trifluoromethanesulfonic anhydride (10.5 ml, 63 mmol) in dichloroethane (30 mL) to N,N-dimethylacrylamide (6.4 L, 63 mmol) in dichloroethane (100 mL) at 0° C. dropwise with vigorous string over 5 minutes. Add indoline (5.6 mL, 50 mmol) in dichloroethane (30 mL) dropwise over 5 minutes. Remove from cooling bath and heat at reflux for 3.5 hours. Cool to room temperature. Dilute with diethyl ether (600 mL). Wash with aqueous potassium carbonate (400 mL), dilute aqueous sodium bicarbonate (2×300 mL) and saturated aqueous sodium chloride (300 mL). Dry over sodium sulfate and concentrate under reduced pressure. Subject the residue to chromatography (pre-packed silica gel), eluting with 19:1 dichloromethane/ethyl acetate to provide the desired compound (2.65 g, 31%).

Workup

  1. customRemove
  2. temperaturefrom cooling bath
  3. temperatureheat
  4. temperatureat reflux for 3.5 hours
  5. additionDilute with diethyl ether (600 mL)
  6. washWash with aqueous potassium carbonate (400 mL), dilute aqueous sodium bicarbonate (2×300 mL) and saturated aqueous sodium chloride (300 mL)
  7. dry with materialDry over sodium sulfate
  8. concentrationconcentrate under reduced pressure
  9. washeluting with 19:1 dichloromethane/ethyl acetate

Sources & evidence

ORD record
ord-89cadcb87b31445492490b5c5d579ca6
Source dataset
uspto-grants-2009_02
Patent number
US07491716B2

Reaction notes

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