Triethylamine → HCID 18373051, compound

HRID 375939Notes

Reaction equation

HRID 375939 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[CH:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(N(CC)CC)C>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I.[Pd](Cl)Cl.O1CCCC1>[C:11]([C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[CH:7][C:6]=2[CH:10]=1)#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 129971-DecyneHCID 27765785-Bromo-1-benzothiophene

Product 1

HCID 18373051HCID 18373051, compoundYield 89%

Reagents, catalysts & solvents 4

HCID 24290Palladium ChlorideCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst2×HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromobenzothiophene (50.0 g), 1-decyne (35.7 g), triethylamine (71.2 g) and dry tetrahydrofuran (150 ml), under nitrogen, was added bis(triphenylphosphine)palladium (II) chloride (1.65 g) followed by copper (I) iodide (0.233 g) with stirring, at room temperature. The reaction mixture was covered with foil and stirred at reflux, under nitrogen, over the weekend. Additional bis-triphenylphosphine)palladium (II) chloride (0.5%) and 0.25% copper (I) iodide were added, and the reaction mixture was stirred at reflux for three days, cooled, filtered through a bed of celite and the filter cake was washed with ether. The residue was flash chromatographed (silica, 1% ethyl acetate-heptane). The appropriate fractions were collected and evaporated to give 56.3 g (89%) of product.

Workup

  1. stirringstirred
  2. temperatureat reflux, under nitrogen, over the weekend
  3. stirringthe reaction mixture was stirred
  4. temperatureat reflux for three days
  5. temperaturecooled
  6. filtrationfiltered through a bed of celite
  7. washthe filter cake was washed with ether
  8. customchromatographed (silica, 1% ethyl acetate-heptane)
  9. customThe appropriate fractions were collected
  10. customevaporated

Sources & evidence

ORD record
ord-93986d9633a54be09ab2702d542fc5a1
Source dataset
uspto-grants-1996_01
Patent number
US05488061

Reaction notes

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