Cesium carbonate → HCID 58408271, compound

HRID 2192282Notes

Reaction equation

HRID 2192282 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][N:4]=1.Br[C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([S:24]([C:27]1[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=1)(=[O:26])=[O:25])[CH2:19][CH2:18]2.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[N:4]=[CH:5][C:6]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([S:24]([C:27]2[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH2:19][CH2:18]3)=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 251342782-(Trifluoromethyl)pyridine-5-boronic AcidHCID 58408289HCID 58408289, compound

Product 1

HCID 58408271HCID 58408271, compoundYield 62.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

236.5 mg 2-(Trifluormethyl)pyridin-5-ylboronic acid, 300.0 mg 4-(5-Bromo-2,3-dihydro-indole-1-sulfonyl)-benzonitrile and 807.4 mg cesium carbonate were dissolved in a mixture of 3 ml water and 10 ml dimethylformamide. The reaction mixture was degassed with argon and then 47.7 mg tetrakis(triphenylphosphine)palladium(0) were added and the mixture heated to 90° C. for two hours. The cooled reaction mixture was diluted with 100 ml ethyl acetate and washed with 50 ml water and brine. The organic layer was dried over MgSO4 and the solvent removed in vacuo. The resulting crude material was purified by purified by chromatography on silica gel to obtain 223 mg 4-[5-(6-Trifluoromethyl-pyridin-3-yl)-2,3-dihydro-indole-1-sulfonyl]-benzonitrile.

Workup

  1. customThe reaction mixture was degassed with argon
  2. addition47.7 mg tetrakis(triphenylphosphine)palladium(0) were added
  3. customThe cooled reaction mixture
  4. washwashed with 50 ml water and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. customthe solvent removed in vacuo
  7. customThe resulting crude material was purified
  8. customby purified by chromatography on silica gel

Sources & evidence

ORD record
ord-812bf69673474815b901d905be4fff71
Source dataset
uspto-grants-2012_12
Patent number
US08329725B2

Reaction notes

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