Trimethylsilylacetylene → HCID 87585669, compound

HRID 729230Notes

Reaction equation

HRID 729230 reaction equation
I[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[NH:7][CH:8]=[O:9].[C:10]([Si:12]([CH3:15])([CH3:14])[CH3:13])#[CH:11]>CN(C=O)C.C(N(CC)CC)C.[Cu]I.C1(P([Pd](Cl)(Cl)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:13][Si:12]([C:10]#[C:11][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[NH:7][CH:8]=[O:9])([CH3:15])[CH3:14]

Participants

7

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 87586268HCID 87586268, compound

Product 1

HCID 87585669HCID 87585669, compoundYield 95.3%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178479802HCID 178479802, compoundCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

The product from step A (37.8 g) was dissolved in a mixture of DMF (500 ml) and triethylamine (50 ml). CuI (1.4 g) and bis(triphenylphosphino)palladiumdichloride (5.2 g) were added under nitrogen and after 15 minutes ethinyl trimethylsilane (22 g) was added dropwise. After 6 hours the solvents were removed under vacuum and the residue was chromatographed on silica gel (hexane:ethyl acetate 2:1) to yield 2-(trimethylsilylethinyl)-3-formamido-thiophene (31.78 g) (m.p. 87-93° C.).

Workup

  1. additionwas added dropwise
  2. customAfter 6 hours the solvents were removed under vacuum
  3. customthe residue was chromatographed on silica gel (hexane:ethyl acetate 2:1)

Sources & evidence

ORD record
ord-45db47693dc64f1a8ba901b39e242d89
Source dataset
uspto-grants-2009_09
Patent number
US07582589B2

Reaction notes

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