HCID 59381950, compound → HCID 59381925, compound

HRID 2354571Notes

Reaction equation

HRID 2354571 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:18]=[C:17]3I)[CH:10]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:40]([Cu])#[N:41]>O1CCOCC1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:18]=[C:17]3[C:40]#[N:41])[CH:10]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 59381950HCID 59381950, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 59381925HCID 59381925, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-(1-benzenesulfonyl-3-iodo-1H-indol-5-yl)-3-benzyl-piperazine-1-carboxylic acid tert-butyl ester (0.23 g, 0.4 mmol), CuCN (0.13 g, 1.4 mmol), Pd2(dibenzylideneacetone)3 (0.017 g, 0.02 mmol), 1,1′-bis(diphenylphosphino)ferrocene (0.040 g, 0.07 mmol) was taken up in 5 mL 1,4 dioxane and warmed to reflux for one hour. The mixture was cooled to room temperature and filtered through a pad of celite. The filter cake was washed with EtOAc and the filtrate was concentrated under reduced pressure. Purification via flash chromatography (gradient: 15 to 25% EtOAc in hexanes) afforded 4-(1-benzenesulfonyl-3-cyano-1H-indol-5-yl)-3-benzyl-piperazine-1-carboxylic acid tert-butyl ester (0.20 g, 97%) as a white foam; MS (M+H)=557.

Workup

  1. temperaturewarmed
  2. temperatureto reflux for one hour
  3. filtrationfiltered through a pad of celite
  4. washThe filter cake was washed with EtOAc
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customPurification via flash chromatography (gradient: 15 to 25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-06992f24f5f8440b8b23056a3e897d48
Source dataset
uspto-grants-2010_07
Patent number
US07754721B2

Reaction notes

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