Tetrabutylammonium Fluoride → 5-(3-chloro-4-methoxyphenyl)-3-(1H-indol-5-yl)-1,2,4-oxadiazole

HRID 710297Notes

Reaction equation

HRID 710297 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:5]([O:7][NH:8][C:9]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)=[NH:10])=O.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:7][N:8]=[C:9]([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][CH:19]=3)[NH:16][CH:15]=[CH:14]4)[N:10]=2)[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178491635HCID 178491635, compound

Product 1

HCID 667266895-(3-chloro-4-methoxyphenyl)-3-(1H-indol-5-yl)-1,2,4-oxadiazoleYield 92.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of the product of Step D (0.4 g; 1.16 mmol) and 1M TBAF in THF (0.5 ml) in anhydrous toluene (10 ml) was refluxed for 3 h under N2, cooled to room temperature and solvents were removed under reduced pressure. The residue was washed with H2O (5 ml) and the solid was purified by FCC (SiO2; CH2Cl2) to give the title compound (0.35 g; 92%) as colourless solid. 1H-NMR (CDCl3) 4.0 (s, 3H); 6.66 (m, 1H); 7.05 (d, 1H, J=8.7 Hz); 7.27 (m, 1H); 7.49 (d, 1H, J=8.7 Hz); 7.97-8.01 (m, 1H); 8.1-8.13 (m, 1H); 8.27 (d, 1H, J=2.1 Hz); 8.3 (broad s, 1H); 8.48 (m, 1H).

Workup

  1. temperaturewas refluxed for 3 h under N2
  2. customsolvents were removed under reduced pressure
  3. washThe residue was washed with H2O (5 ml)
  4. customthe solid was purified by FCC (SiO2; CH2Cl2)

Sources & evidence

ORD record
ord-b4f202a81a64435493b81b4d802b2887
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

Loading…