Trimethylsilylacetylene → HCID 90418779, compound

HRID 588269Notes

Reaction equation

HRID 588269 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[Si:12]([C:16]#[CH:17])([CH3:15])([CH3:14])[CH3:13]>CN(C=O)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>[CH3:13][Si:12]([C:16]#[C:17][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2)([CH3:15])[CH3:14]

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 98380455-Iodoindolin-2-one

Product 1

HCID 90418779HCID 90418779, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
0 °C

Procedure

To a solution of 5-iodoindolin-2-one (518 mg, 2 mmol), TEA (3 ml) and CuI (38 mg) in DMF (3 ml) was added to PdCl2(PPh3)2 (70 mg). The mixture was cooled to 0° C. and a solution of TMS-acetylene (1 ml). The mixture was maintained same temperature for 3 h, then warmed to rt. After stirring for overnight, the reaction mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography to give 5-((trimethylsilyl)ethynyl)indolin-2-one (451 mg).

Workup

  1. temperatureThe mixture was maintained same temperature for 3 h
  2. temperaturewarmed to rt
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4e581d966bb440af8cc3ea059d0962b5
Source dataset
uspto-grants-2016_01
Patent number
US09227962B2

Reaction notes

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