Tetrahydrofuran → 1-(4-Methylphenylsulfonyl)-5-(1-dodecynyl)indole-3-carboxaldehyde

HRID 2379230Notes

Reaction equation

HRID 2379230 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16](Br)=[CH:17][CH:18]=3)[C:13]([CH:21]=[O:22])=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH:23]#[C:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].O1CC[CH2:35][CH2:34]1>C(N(CC)CC)C.[Cu](I)I.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>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:23]#[C:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:34][CH3:35])=[CH:17][CH:18]=3)[C:13]([CH:21]=[O:22])=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 129971-DecyneHCID 103849695-bromo-1-(4-methylbenzenesulfonyl)-1H-indole-3-carbaldehyde

Product 1

HCID 183729391-(4-Methylphenylsulfonyl)-5-(1-dodecynyl)indole-3-carboxaldehydeYield 50.8%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
65 °C

Procedure

To a degassed mixture of 1-(4-methylphenylsulfonyl)-5-bromoindole-3-carboxaldehyde (36.9 g), 1-decyne (16.8 g), in dry triethylamine (200 ml) and dry tetrahydrofuran (150 ml) was added, 1 mole percent of copper (II) iodide and 2 mole percent of bis(triphenylphosphine)palladium (II) chloride. The reaction mixture was stirred at 65° C. for 7 days. The solution was evaporated, and the residue was flash chromatographed (silica gel:4:1, dichloromethane:heptane). The appropriate fractions were collected and evaporated. The residue was recrystallized from hexane to give 23.1 g (50.8%) of product, mp 84°-86° C.

Workup

  1. customThe solution was evaporated
  2. customchromatographed (silica gel:4:1, dichloromethane:heptane)
  3. customThe appropriate fractions were collected
  4. customevaporated
  5. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-7993258df5264e5297896d940bf5235f
Source dataset
uspto-grants-1994_11
Patent number
US05360811

Reaction notes

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