Tetrabutylammonium Fluoride → HCID 46183201, compound

HRID 341292Notes

Reaction equation

HRID 341292 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][C:15](/[CH:19]=[CH:20]/[C:21]4[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=4)=[CH:16][CH:17]=3)[C:12]3[CH:29]=[C:30]([Cl:33])[CH:31]=[N:32][C:11]2=3)(=O)=O)C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:33][C:30]1[CH:31]=[N:32][C:11]2[NH:10][C:18]3[C:13]([C:12]=2[CH:29]=1)=[CH:14][C:15](/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)=[CH:16][CH:17]=3

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 46186442HCID 46186442, compound

Product 1

HCID 46183201HCID 46183201, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a Solution of (E)-9-Benzenesulfonyl-3-Chloro-6-(2′-(4-methoxyphenyl)ethenyl)-9H-pyrido[2,3-b]indole (127 mg, 0.25 mmol, 1 equiv.) in anhydrous THF (11 ml) under Argon, TBAF 1M in THF (1.26 ml, 1.26 mmol, 5 equiv.) is added dropwise. The reaction is carried out at reflux for 4 hours and then concentrated under reduced pressure. The crude product is washed with MeOH and then filtered. The product R350 is obtained as a white solid (17 mg, 0.04 mmol) in 21% yield. 1H NMR (300 MHz, DMSO d6) δ 12.05 (br s, 1H), 8.68 (d, 1H, J=2.1 Hz), 8.42 (d, 1H, J=2.3 Hz), 8.41 (s, 1H), 7.74 (d, 1H, J=8.3 Hz), 7.55 (d, 2H, J=8.5 Hz), 7.50 (d, J=8.3 Hz), 7.21 (d, 2H, J=1.5 Hz), 6.97 (d, 2H, J=8.5 Hz), 3.78 (s, 3H).

Workup

  1. temperatureat reflux for 4 hours
  2. concentrationconcentrated under reduced pressure
  3. washThe crude product is washed with MeOH
  4. filtrationfiltered

Sources & evidence

ORD record
ord-c817eed9b6ce478091cc0bf1ad8c5ed2
Source dataset
uspto-grants-2014_11
Patent number
US08895744B2

Reaction notes

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