Water → HCID 66954001, compound

HRID 2096968Notes

Reaction equation

HRID 2096968 reaction equation
[CH3:1][C:2](C)([O-])C.[K+].[Br:7][C:8]1[CH:9]=[C:10]2[NH:16][C:15](=[O:17])[CH2:14][C:11]2=[N:12][CH:13]=1.[C:18]([O:22]C)(=O)[CH:19]=[CH2:20].O>CS(C)=O.C(OCC)(=O)C>[Br:7][C:8]1[CH:9]=[C:10]2[NH:16][C:15](=[O:17])[C:14]3([CH2:20][CH2:19][C:18](=[O:22])[CH2:2][CH2:1]3)[C:11]2=[N:12][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7294Methyl AcrylateHCID 23665647Potassium tert-butoxide2×HCID 469416416-Bromo-1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one

Product 1

HCID 66954001HCID 66954001, compoundYield 753%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium tert-butoxide (0.03 g, 0.27 mmol) was added to a suspension of 6-bromo-1H-pyrrolo[3,2-b]pyridin-2(3H)-one (preparation 16c, 0.87 g, 4.1 mmol) in dimethylsulphoxide (4 mL) and, after stirring for 10 minutes at room temperature, the mixture was heated to 40-45° C. and methyl acrylate (1.14 mL, 12.71 mmol) was added dropwise over 60 minutes. After the addition, the mixture was stirred for 2 hours and then further potassium tert-butoxide (1.4 g, 12.21 mmol) was added portionwise over 30 minutes keeping the temperature below 50° C. The mixture was then heated to 100° C. and stirred for 2 hours. Water (20 mL) was added and heating was continued at 85° C. for 2 hours and then the mixture was left to cool overnight. Ethyl acetate was added and the organic layer was washed with water, brine, dried (MgSO4) and evaporated to give the title compound (0.60 g, 50%) as a white solid.

Workup

  1. temperaturethe mixture was heated to 40-45° C.
  2. additionAfter the addition
  3. stirringthe mixture was stirred for 2 hours
  4. customthe temperature below 50° C
  5. temperatureThe mixture was then heated to 100° C.
  6. stirringstirred for 2 hours
  7. temperatureheating
  8. waitwas continued at 85° C. for 2 hours
  9. waitthe mixture was left
  10. temperatureto cool overnight
  11. washthe organic layer was washed with water, brine
  12. dry with materialdried (MgSO4)
  13. customevaporated

Sources & evidence

ORD record
ord-e4e51298e78845e5b43d60e865d78908
Source dataset
uspto-grants-2013_05
Patent number
US08450341B2

Reaction notes

Loading…