Methanesulfonic acid 5-[1-(4-bromo-phenyl)-1H-indol-5-yl]-pent-4-ynyl ester → Methanesulfonic acid 5-[1-(4-bromo-phenyl)-1H-indol-5-yl]-pentyl ester

HRID 1633661Notes

Reaction equation

HRID 1633661 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]#[C:18][CH2:19][CH2:20][CH2:21][O:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1>CCOC(C)=O.CCO.CCCCCC.O=[Pt]=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][S:23]([CH3:26])(=[O:24])=[O:25])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86585589Methanesulfonic acid 5-[1-(4-bromo-phenyl)-1H-indol-5-yl]-pent-4-ynyl ester

Product 1

HCID 86585590Methanesulfonic acid 5-[1-(4-bromo-phenyl)-1H-indol-5-yl]-pentyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 21875506EtOAc EtOH hexaneSolvent

Procedure

432 mg (1 mmol) Methanesulfonic acid 5-[1-(4-bromo-phenyl)-1H-indol-5-yl]-pent-4-ynyl ester in 30 ml EtOAc/EtOH/hexane (1:1:1) was hydrogenated in the presence of 20 mg PtO2, the solution was filtered and evaporated. Column chromatography on silica gel with hexane/EtOAc 4:1 yielded (95%) Methanesulfonic acid 5-[1-(4-bromo-phenyl)-1H-indol-5-yl]-pentyl ester as colorless viscous oil, MS: 435 (M, 1Br).

Workup

  1. filtrationthe solution was filtered
  2. customevaporated

Sources & evidence

ORD record
ord-121b0ce93cc848b6992e73bb9df64544
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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