Tetrahydrofuran → HCID 86623275, compound

HRID 556134Notes

Reaction equation

HRID 556134 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:16])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10](I)=[CH:9][CH:8]=3.C1COCC1.CCN(CC)CC.[CH3:29][Si:30]([C:33]#[CH:34])([CH3:32])[CH3:31]>CCOCC.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.[Cu]I>[CH3:29][Si:30]([C:33]#[C:34][C:4]1[C:5]2[N:6]([CH3:16])[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13]=2[CH:14]=[CH:2][CH:3]=1)([CH3:32])[CH3:31]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 13899208HCID 13899208, compound

Product 1

HCID 86623275HCID 86623275, compoundYield 135.6%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

Firstly, a mixture of PdCl2(PPh3)2 (13 mg, 0.018 mmol), CuI (3.5 mg, 0.018 mmol) and 3,6-diiodo-9-methylcarbazole (200 mg, 0.46 mmol) was added with dist. THF (3 mL), dist. Et3N (1.5 mL) and trimethylsilylacetylene (653 μL, 4.6 mmol). The resultant mixture was stirred under a nitrogen atmosphere at room temperature for 3 hours to obtain a reaction mixture. Then, the reaction mixture was diluted with ether. After that, an organic layer was washed with dist. H2O and sat. NaCl, and was dried with MgSO4. The dried organic layer was filtered and concentrated to obtain a crude product. Subsequently, the obtained crude product was separated and purified by silica gel column chromatography (hexane/EtOAc=5/1) to obtain 3,6-bis[(trimethylsilylethynyl)-9-methylcarbazole (173 mg, 100% yield).

Workup

  1. additionwas added with dist
  2. customto obtain a reaction mixture
  3. washAfter that, an organic layer was washed with dist
  4. dry with materialH2O and sat. NaCl, and was dried with MgSO4
  5. filtrationThe dried organic layer was filtered
  6. concentrationconcentrated
  7. customto obtain a crude product
  8. customSubsequently, the obtained crude product
  9. customwas separated
  10. custompurified by silica gel column chromatography (hexane/EtOAc=5/1)

Sources & evidence

ORD record
ord-c7b29ef1d94243978141ec849342820a
Source dataset
uspto-grants-2011_11
Patent number
US08053588B2

Reaction notes

Loading…