Trifluoromethanesulfonic acid → 6-Methoxy-2'-oxo-1',2'-dihydrospiro[1-benzofuran-3,3'-indole]-5-carbonitrile

HRID 1407632Notes

Reaction equation

HRID 1407632 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]#[N:10])=[CH:7][C:6]2[C:11]3([CH2:30][O:31][C:5]=2[CH:4]=1)[C:19]1[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=1)[N:13](CC1C=CC(OC)=CC=1)[C:12]3=[O:29].FC(F)(F)S(O)(=O)=O>ClCCl.FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]1[C:8]([C:9]#[N:10])=[CH:7][C:6]2[C:11]3([CH2:30][O:31][C:5]=2[CH:4]=1)[C:19]1[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=1)[NH:13][C:12]3=[O:29]

Participants

5

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 593526926-Methoxy-1'-(4-methoxybenzyl)-2'-oxo-1',2'-dihydrospiro[1-benzofuran-3,3'-indole]-5-carbonitrile

Product 1

HCID 593524576-Methoxy-2'-oxo-1',2'-dihydrospiro[1-benzofuran-3,3'-indole]-5-carbonitrileYield 96.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirred solution of 6-methoxy-1′-(4-methoxybenzyl)-2′-oxo-1′,2′-dihydrospiro[1-benzofuran-3,3′-indole]-5-carbonitrile (0.50 g, 1.2 mmol) in dichloromethane (5 mL) and trifluoroacetic acid (5 mL) was added trifluoromethanesulfonic acid (1.0 mL, 11 mmol). The reaction mixture was stirred at ambient temperature for 18 h and concentrated in vacuo. The residue was basified with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography to afford 6-methoxy-2′-oxo-1′,2′-dihydrospiro[1-benzofuran-3,3′-indole]-5-carbonitrile (0.34 g, 96%): mp 185-186° C.; 1H NMR (300 MHz, CDCl3) δ 8.46 (s, 1H), 7.30-7.25 (m, 1H), 7.11-7.03 (m, 2H), 6.97-6.94 (m, 2H), 6.56 (s, 1H), 4.91 (ABq, 2H), 3.90 (s, 3H); MS (ES+) m/z 292.9 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-388017222c6a4088b19a5e0983f11d17
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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