Cesium carbonate → HCID 58408270, compound

HRID 2192279Notes

Reaction equation

HRID 2192279 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:15]1[CH:16]=[C:17]2[CH2:23][C:22](=[O:24])[NH:21][C:18]2=[N:19][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O.CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([C:15]2[CH:16]=[C:17]3[CH2:23][C:22](=[O:24])[NH:21][C:18]3=[N:19][CH:20]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 155040625-bromo-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-one

Product 1

HCID 58408270HCID 58408270, compoundYield 12.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

8.13 g 4-(Trifluormethyl)phenyl-boronic acid, 7.6 g 5-Bromo-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one and 34.9 cesium carbonate were dissolved in a mixture of 14 ml water and 42 ml dimethylformamide. The reaction mixture was degassed with argon and then 2.0 g tetrakis(triphenylphosphine)palladium(0) were added and the mixture heated to 100° C. for two hours. Then 1.0 g 4-(Trifluormethyl)phenyl-boronic acid were added and the mixture stirred for an additional hour. Then 1.0 g 4-(Trifluormethyl)phenyl-boronic acid were added and the mixture stirred for additional three hours at 100° C. The cooled reaction mixture was diluted with 500 ml ethyl acetate and washed with 300 ml water and brine. The organic layer was dried over MgSO4 and the solvent removed in vacuo. The resulting crude material was purified by chromatography on silica gel to obtain 1.2 g 5-(4-Trifluoromethyl-phenyl)-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one.

Workup

  1. customThe reaction mixture was degassed with argon
  2. addition2.0 g tetrakis(triphenylphosphine)palladium(0) were added
  3. additionThen 1.0 g 4-(Trifluormethyl)phenyl-boronic acid were added
  4. additionThen 1.0 g 4-(Trifluormethyl)phenyl-boronic acid were added
  5. stirringthe mixture stirred for additional three hours at 100° C
  6. customThe cooled reaction mixture
  7. washwashed with 300 ml water and brine
  8. dry with materialThe organic layer was dried over MgSO4
  9. customthe solvent removed in vacuo
  10. customThe resulting crude material was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-61d21b010b4044e19c2b8eb4273865bc
Source dataset
uspto-grants-2012_12
Patent number
US08329725B2

Reaction notes

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