Iodobenzene → HCID 69663474, compound

HRID 2212102Notes

Reaction equation

HRID 2212102 reaction equation
[C:1]1([S:7]([C:10]([CH3:23])([CH3:22])[CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH:16]([C:20]#[CH:21])[CH2:15]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(NC(C)C)(C)C.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>[C:1]1([S:7]([C:10]([CH3:23])([CH3:22])[CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][CH:16]([C:20]#[C:21][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:15]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 11575IodobenzeneHCID 21048806HCID 21048806, compound

Product 1

HCID 69663474HCID 69663474, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 7912DiisopropylamineSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-(4-benzenesulfonyl-4-methylpentyl)-3-ethynylpiperidine (0.33 g, 1.0 mmol), iodobenzene (80 μL, 0.7 mmol), dichlorobis(triphenylphosphine)palladium(II) (35 mg, 0.05 mmol) and copper(I) iodide (6 mg, 0.03 mmol) in diisopropylamine (5 ml) was stirred at 70° C. for 2 hours. The reaction mixture was filtered through Celite, washing with dichloromethane (50 ml). The filtrate was concentrated in vacuo and the residue purified by flash column chromatography on silica gel, eluting with 2% methanol/dichloromethane, followed by an SCX cartridge and finally preparative thin layer chromatography, eluting with 7% methanol/dichloromethane, to give the title compound. The hydrochloride salt (63 mg, 14%) was obtained by treatment with ethereal hydrogen chloride and crystallisation from ethanol/diethyl ether.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashing with dichloromethane (50 ml)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue purified by flash column chromatography on silica gel
  5. washeluting with 2% methanol/dichloromethane
  6. washeluting with 7% methanol/dichloromethane

Sources & evidence

ORD record
ord-f271806f0834401ebf6175ac5dd5a6fe
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

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