Sodium Bicarbonate → HCID 67343575, compound

HRID 1673419Notes

Reaction equation

HRID 1673419 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.C1(CNCC2CCCCC2)CCCCC1.[C:27]([NH:35][C:36]1[CH:48]=[C:47]([CH:49]=[CH2:50])[CH:46]=[CH:45][C:37]=1[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.CN(C)C(=O)C>[C:27]([NH:35][C:36]1[CH:48]=[C:47](/[CH:49]=[CH:50]/[C:2]2[CH:10]=[C:9]3[C:5]([CH2:6][C:7](=[O:11])[NH:8]3)=[CH:4][CH:3]=2)[CH:46]=[CH:45][C:37]=1[C:38]([O:40][C:41]([CH3:43])([CH3:44])[CH3:42])=[O:39])(=[O:34])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 27732896-bromo-2,3-dihydro-1H-indol-2-oneHCID 4594378Bis(cyclohexylmethyl)amineHCID 67343635Tert-butyl 2-(benzamido)-4-vinylbenzoate

Product 1

HCID 67343575HCID 67343575, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

0.20 g of 6-bromo-2-oxoindoline, 0.40 mL of N,N-dicyclohexylmethylamine and 18 mg of trans-di(μ-acetato)bis-o-(di-o-tolylphosphino)benzyl dipalladium(II) were added to 2.0 mL of N,N-dimethylacetamide solution containing 0.46 g of tert-butyl 2-(benzamido)-4-vinylbenzoate at room temperature and stirred under nitrogen atmosphere at 110° C. for 7 hours. After the reaction mixture was cooled to room temperature, a saturated sodium hydrogen carbonate aqueous solution and ethyl acetate were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 10% citric acid aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia chemical Ltd., eluent; hexane:ethyl acetate=1:1] to obtain 0.15 g of tert-butyl 2-(benzamido)-4-((E)-2-(2-oxoindolin-6-yl)vinyl)benzoate as green solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. washafter washed with 10% citric acid aqueous solution
  5. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia chemical Ltd., eluent; hexane:ethyl acetate=1:1]

Sources & evidence

ORD record
ord-61aa3c259f8146dead71005abd7dc296
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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