Trimethylsilylacetylene → HCID 59457700, compound

HRID 1711099Notes

Reaction equation

HRID 1711099 reaction equation
[F:1][C:2]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12](I)[S:13][C:6]=12.[C:22]([Si:24]([CH3:27])([CH3:26])[CH3:25])#[CH:23]>C1COCC1.[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>[F:1][C:2]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:23]#[C:22][Si:24]([CH3:27])([CH3:26])[CH3:25])[S:13][C:6]=12

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 594576617-(2-Fluoro-4-nitrophenoxy)-2-iodothieno[3,2-b]pyridine

Product 1

HCID 59457700HCID 59457700, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the iodide 408 (4.5 g, 10.8 mmol) in dry THF (120 ml) at was added CuI (205 mg, 0.1 eq, 1.08 mmol), TEA (2.73 g, 2.5 eq, 27 mmol), ethynyltrimethylsilane (2.12 g, 2 eq, 21.6 mmol) and Pd(PPh3)2Cl2 (212 mg, 0.028 eq, 0.30 mmol) and the reaction mixture was heated to reflux for 2 hours. It was then cooled to RT and partitioned between EtOAc and water. The organic phase was collected, dried over anhydrous sodium sulfate, filtered and adsorbed onto silica gel. Purification by column chromatography (30% EtOAc/hexane) afforded 409 (2.2 g, 53% yield). LCMS: 387.1 (M+H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. custompartitioned between EtOAc and water
  4. customThe organic phase was collected
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customPurification by column chromatography (30% EtOAc/hexane)

Sources & evidence

ORD record
ord-235cdba7cc8947108ab901a4e0f4a737
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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