Hydrochloric Acid → (Z)-6-methoxy-7-(piperazin-1-ylmethyl)-2-[(1-tosyl-1H-indol-3-yl)methylene]benzofuran-3(2H)-one

HRID 1749839Notes

Reaction equation

HRID 1749839 reaction equation
[CH3:1][O:2][C:3]1[CH:32]=[CH:31][C:6]2[C:7](=[O:30])/[C:8](=[CH:10]/[C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]([S:20]([C:23]4[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[CH:12]=3)/[O:9][C:5]=2[C:4]=1[CH2:33][N:34]1[CH2:39][CH2:38][N:37](C(OC(C)(C)C)=O)[CH2:36][CH2:35]1.Cl>C(Cl)Cl.O1CCOCC1>[CH3:1][O:2][C:3]1[CH:32]=[CH:31][C:6]2[C:7](=[O:30])/[C:8](=[CH:10]/[C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]([S:20]([C:23]4[CH:24]=[CH:25][C:26]([CH3:27])=[CH:28][CH:29]=4)(=[O:22])=[O:21])[CH:12]=3)/[O:9][C:5]=2[C:4]=1[CH2:33][N:34]1[CH2:35][CH2:36][NH:37][CH2:38][CH2:39]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86682012tert-butyl (Z)-4-({6-methoxy-3-oxo-2-[(1-tosyl-1H-indol-3-yl)methylene]-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate

Product 1

HCID 71278631(Z)-6-methoxy-7-(piperazin-1-ylmethyl)-2-[(1-tosyl-1H-indol-3-yl)methylene]benzofuran-3(2H)-oneYield 35.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (Z)-4-({6-methoxy-3-oxo-2-[(1-tosyl-1H-indol-3-yl)methylene]-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.0400 g, 0.0621 mmol) in methylene chloride (2 mL) was added with a 4 N solution of hydrogen chloride in 1,4-dioxane (2 mL), and the mixture was stirred at room temperature for 11 hours. The reaction mixture was concentrated, the resulting residue was added with saturated aqueous sodium hydrogencarbonate, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and then the solvent was evaporated to obtain (Z)-6-methoxy-7-(piperazin-1-ylmethyl)-2-[(1-tosyl-1H-indol-3-yl)methylene]benzofuran-3(2H)-one (0.0121 g, 35%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe resulting residue was added with saturated aqueous sodium hydrogencarbonate
  3. extractionthe mixture was extracted three times with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-010c68c5319b45eea10a75ed8e05dd36
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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