Cesium carbonate → HCID 11155683, compound

HRID 1814152Notes

Reaction equation

HRID 1814152 reaction equation
C[O:2][C:3](=[O:15])[CH2:4][C:5]1[C:6]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:7]=2[S:8][CH:9]=1.[F:16][C:17]([F:35])([F:34])[C:18]1[CH:33]=[CH:32][C:21]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30]Cl)=[CH:26][CH:25]=2)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(C#N)(C)=O.CCOCC>[F:16][C:17]([F:34])([F:35])[C:18]1[CH:33]=[CH:32][C:21]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][O:14][C:11]3[CH:12]=[CH:13][C:6]4[C:5]([CH2:4][C:3]([OH:2])=[O:15])=[CH:9][S:8][C:7]=4[CH:10]=3)=[CH:26][CH:25]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 20765985(6-Hydroxy-benzo[b]thiophen-3-yl)acetic acid methyl esterHCID 22280095HCID 22280095, compound

Product 1

HCID 11155683HCID 11155683, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 694302-OxopropiononitrileSolvent

Procedure

Compounds 5C, 5E and cesium carbonate in 10 mL AcCN stirred at 60° C. for 18 hours. The reaction was then cooled, diluted with Et2O and filtered through Celite®. The filtrate was collected and concentrated in vacuo. Recrystalisation from CHCl3/Hexanes gave 340 mg (62%) of the title compound. MS m/z 487 (M+1).

Workup

  1. temperatureThe reaction was then cooled
  2. filtrationfiltered through Celite®
  3. customThe filtrate was collected
  4. concentrationconcentrated in vacuo
  5. customRecrystalisation from CHCl3/Hexanes

Sources & evidence

ORD record
ord-67e6a40856ba481795e547fdc7d096cc
Source dataset
uspto-grants-2005_04
Patent number
US06875780B2

Reaction notes

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