Water → HCID 66953983, compound

HRID 1619111Notes

Reaction equation

HRID 1619111 reaction equation
[CH3:1][C:2](C)([O-])C.[K+].[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([CH2:12][C:13](=[O:17])[NH:14]2)=[CH:10][CH:9]=1.[C:18]([O:22]C)(=O)[CH:19]=[CH2:20].O>CS(C)=O>[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]3([CH2:20][CH2:19][C:18](=[O:22])[CH2:2][CH2:1]3)[C:13](=[O:17])[NH:14]2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7294Methyl AcrylateHCID 27732896-bromo-2,3-dihydro-1H-indol-2-oneHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 66953983HCID 66953983, compoundYield 828.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium tert-butoxide (0.085 g, 0.8 mmol) was added to a suspension of 6-bromoindolin-2-one (preparation 1, 3.00 g, 14.2 mmol) in dimethylsulphoxide (7 mL) and, after stirring for 10 minutes at room temperature, the mixture was heated to 40-45° C. and methyl acrylate (4.00 mL, 44.4 mmol) was added dropwise over 70 minutes. After the addition, the mixture was stirred for 1 hour and then further potassium tert-butoxide (3.82 g, 34.0 mmol) was added portionwise over 30 minutes keeping the temperature below 50° C. The mixture was then heated to 100° C. and stirred for 1.5 hours. Water (45 mL) was added and heating was continued at 85° C. for 4 hours and then the mixture was left to cool overnight. The resultant precipitate was filtered and the solid washed with water and hexanes to give the crude product. Recrystallization from ethyl alcohol gave the title compound (1.95 g, 42%) as a white solid.

Workup

  1. temperaturethe mixture was heated to 40-45° C.
  2. additionAfter the addition
  3. stirringthe mixture was stirred for 1 hour
  4. customthe temperature below 50° C
  5. temperatureThe mixture was then heated to 100° C.
  6. stirringstirred for 1.5 hours
  7. temperatureheating
  8. waitwas continued at 85° C. for 4 hours
  9. waitthe mixture was left
  10. temperatureto cool overnight
  11. filtrationThe resultant precipitate was filtered
  12. washthe solid washed with water and hexanes
  13. customto give the crude product
  14. customRecrystallization from ethyl alcohol

Sources & evidence

ORD record
ord-feea7e94f0ef4c958934e01c4ddeedb0
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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