HCID 10411996, compound → HCID 11744377, compound

HRID 505622Notes

Reaction equation

HRID 505622 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C:20]([N:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]2)=O)=[CH:12]1)(=[O:10])=[O:9].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:20][N:22]2[CH2:23][CH2:24][N:25]([CH3:28])[CH2:26][CH2:27]2)=[CH:12]1)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 10411996HCID 10411996, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 11744377HCID 11744377, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(1-(2-Bromobenzenesulfonyl)-1H-indol-3-yl)-(4-methylpiperazin-1-yl)methanone (0.93 g, 0.002 moles) in THF (10 mL) was treated with cooled and stirred suspension of LAH (0.04 g, 0.001 moles) in THF (10 mL) slowly over the period of 2 to 5 hours, the reaction mixture was heated to reflux for 2-4 hours. After the completion of reaction, the reaction mixture was poured on to the ice and the compound was extracted with ethyl acetate. The residue obtained was purified by flash chromatography (silica gel, EtOAc/Hexanes, 2/8) to afford the compound, which was identified by IR, NMR and mass spectral analyses as the title compound.

Workup

  1. temperaturewith cooled
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 2-4 hours
  4. customAfter the completion of reaction
  5. extractionthe compound was extracted with ethyl acetate
  6. customThe residue obtained
  7. customwas purified by flash chromatography (silica gel, EtOAc/Hexanes, 2/8)
  8. customto afford the compound, which

Sources & evidence

ORD record
ord-65a158827e704f7e908080e5af1b8bed
Source dataset
uspto-grants-2010_08
Patent number
US07781476B2

Reaction notes

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