Ethyl Acetate → HCID 118468364, compound

HRID 629319Notes

Reaction equation

HRID 629319 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][N:7]([C@@H:12]3[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]3[OH:18])[C:8]2=[O:11])=[CH:4][CH:3]=1.[Cl-].[Cl:20][C:21]1[N:26]=[CH:25][C:24]([CH2:27][Zn+])=[CH:23][CH:22]=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C1COCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[Cl:20][C:21]1[N:26]=[CH:25][C:24]([CH2:27][C:2]2[CH:10]=[C:9]3[C:5]([CH2:6][N:7]([C@@H:12]4[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]4[OH:18])[C:8]3=[O:11])=[CH:4][CH:3]=2)=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 118468159Rac-6-bromo-2-(trans-2-hydroxycyclohexyl)isoindolin-1-oneHCID 178478124HCID 178478124, compound

Product 1

HCID 118468364HCID 118468364, compound

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of rac-6-bromo-2-(trans-2-hydroxycyclohexyl)isoindolin-1-one (0.23 g) in THF (3.0 mL) were added ((6-chloropyridin-3-yl)methyl)zinc(II) chloride (3.66 mL) and bis(tri-tert-butylphosphine)palladium(0) (0.07 g) under ice-cooling, and the mixture was stirred at room temperature for 3 hr under argon atmosphere. To the reaction mixture were added 5% aqueous sodium bicarbonate and ethyl acetate, the mixture was stirred, and the insoluble substance was removed by filtration. The filtrate was extracted with ethyl acetate, the organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.15 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred
  3. customthe insoluble substance was removed by filtration
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washthe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8a625d899a974308940e79148d13e733
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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