Water → HCID 9948484, compound

HRID 428716Notes

Reaction equation

HRID 428716 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].Br[C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])/[C:11]/2=[CH:18]\[C:19]1[NH:20][CH:21]=[CH:22][CH:23]=1.O>CN(C=O)C.C(N(CC)CC)C.[Cu]I.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>[NH:20]1[CH:21]=[CH:22][CH:23]=[C:19]1/[CH:18]=[C:11]1\[C:12](=[O:17])[NH:13][C:14]2[C:10]\1=[CH:9][C:8]([C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])=[CH:16][CH:15]=2

Participants

8

Reactant 3

HCID 962WaterHCID 66111TrimethylsilylacetyleneHCID 59973116HCID 59973116, compound2×

Product 1

HCID 9948484HCID 9948484, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

(Trimethylsilyl)acetylene (1.36 g,13.8 mmol) (Aldrich) and (Z)-5-bromo-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (2.0 g, 6.9 mmol) (Starting Material 7) were dissolved in 30 mL DMF and 40 mL triethylamine. The solution was degassed for 30 minutes by bubbling argon through the solution. At this time CuI (130 mg, 0.68 mmol) (Aldrich) and (Ph3P)2PdCl2 (400 mg, 0.57 mmol) (Aldrich) were added, and the reaction was heated, under argon, at 70° C. for 22 hours. Water (20 mL) was then added and the precipitate was filtered off and dried. The product was purified via flash column chromatography (SiO2, 230-400 mesh) with 1% MeOH/CHCl3 to give (Z)-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-5-(trimethylsilyl)ethynyl-2H-indol-2-one as a yellow powder. (Yield 1.07 g, 51%).

Workup

  1. customThe solution was degassed for 30 minutes
  2. customby bubbling argon through the solution
  3. filtrationthe precipitate was filtered off
  4. customdried
  5. customThe product was purified via flash column chromatography (SiO2, 230-400 mesh) with 1% MeOH/CHCl3

Sources & evidence

ORD record
ord-0ba02400647342e68c97ebe4d8ec0999
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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