Cesium carbonate → HCID 71252567, compound

HRID 2411635Notes

Reaction equation

HRID 2411635 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][N:19]=3)[CH2:14][CH2:13]2)=[O:11])=[C:6]([CH:9]=1)[C:7]#[N:8].[S:26]1(=[O:32])(=[O:31])[CH2:30][CH2:29][CH2:28][NH:27]1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>[Cl-].[Na+].O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[CH3:24][C:23]1[C:18]([N:15]2[CH2:16][CH2:17][N:12]([C:10]([C:5]3[CH:4]=[CH:3][C:2]([N:27]4[CH2:28][CH2:29][CH2:30][S:26]4(=[O:32])=[O:31])=[CH:9][C:6]=3[C:7]#[N:8])=[O:11])[CH2:13][CH2:14]2)=[N:19][CH:20]=[C:21]([CH3:25])[CH:22]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 6421571,3-PropanesultamHCID 584846285-Bromo-2-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]benzonitrile

Product 1

HCID 71252567HCID 71252567, compoundYield 71.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of 5-bromo-2-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]benzonitrile (599 mg) described in Preparation Example 187, isothiazolidine 1,1-dioxide (236 mg), 4,5-bisdiphenylphosphanyl-9,9-dimethyl-9H-xanthene (130 mg), palladium acetate (34 mg) and cesium carbonate (733 mg) was added 1,4-dioxane (2 mL), and the mixture was stirred with heating under reflux for 2 hr. The reaction mixture was cooled, saturated brine was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (ethyl acetate:hexane) to give the title compound (470 mg).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 2 hr
  3. temperatureThe reaction mixture was cooled
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by column chromatography (ethyl acetate:hexane)

Sources & evidence

ORD record
ord-36734feec01f4533bb167c5ff246fb3f
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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