Hydrochloric Acid → HCID 58239409, compound

HRID 2390965Notes

Reaction equation

HRID 2390965 reaction equation
CC(C)([O-])C.[K+].[C:7]([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])#[N:8].Br[C:18]1[CH:19]=[CH:20][C:21]2[S:25][CH:24]=[CH:23][C:22]=2[CH:26]=1.Cl>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[BH4-].[Na+].O.COCCOC>[S:25]1[C:21]2[CH:20]=[CH:19][C:18]([CH:9]([C:7]#[N:8])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:26][C:22]=2[CH:23]=[CH:24]1

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 70693tert-Butyl cyanoacetateHCID 27765785-Bromo-1-benzothiopheneHCID 23665647Potassium tert-butoxide

Product 1

HCID 58239409HCID 58239409, compoundYield 88.7%

Reagents, catalysts & solvents 5

HCID 11776TriphenylphosphineCatalystHCID 4311764Sodium borohydrideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To 1,2-dimethoxyethane (25 mL) suspension of 0.16 g of dichlorobis(triphenylphosphine)palladium(II) were added 0.12 g of triphenylphosphine, 0.01 g of sodium borohydride, 5.53 g of potassium tert-butoxide and 3.48 g of tert-butyl cyanoacetate, which was then stirred at room temperature for 10 minutes. Thereto was added 5.00 g of 5-bromobenzothiophene, which was then refluxed for 2 hours. After to the reaction mixture was added 15 mL of water, the pH was adjusted to 1 with 2 mL of hydrochloric acid. The precipitate was collected by filtration to provide 5.69 g of tert-butyl 2-(1-benzothiophen-5-yl)-2-cyanoacetate as pale yellow solid form.

Workup

  1. temperaturewas then refluxed for 2 hours
  2. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-fa511c941ea843d08d375cb5bcd421a0
Source dataset
uspto-grants-2012_09
Patent number
US08273902B2

Reaction notes

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