Tetrabutylammonium Fluoride → HCID 24803271, compound

HRID 2197441Notes

Reaction equation

HRID 2197441 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]=[C:9]([CH:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:28])[CH2:18][N:19]3[CH:23]=[C:22]([Si](C)(C)C)[N:21]=[N:20]3)[CH2:13][CH2:12]2)[O:8][N:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]=[C:9]([CH:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:28])[CH2:18][N:19]3[CH:23]=[CH:22][N:21]=[N:20]3)[CH2:13][CH2:12]2)[O:8][N:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58295847HCID 58295847, compound

Product 1

HCID 24803271HCID 24803271, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

38 mg (1 eq.) of the 1-[4-(3-thiophen-2-yl[1,2,4]oxadiazol-5-yl)piperid-1-yl]-2-(4-trimethylsilanyl[1,2,3]triazol-1-yl)ethanone obtained above in the preceding step and 100 μl (1.05 eq.) of tetrabutylammonium fluoride were dissolved in 0.9 ml of THF in a sealed tube, and then refluxed for 1 hour. After cooling to room temperature, the THF was evaporated off and the residue was then purified on silica gel (90/10 CH2Cl2/methanol). 1-[4-(3-Thiophen-2-yl[1,2,4]oxadiazol-5-yl)piperid-1-yl]-2-[1,2,3]triazol-1-ylethanone was obtained in the form of a pale yellow solid, in a yield of 48%.

Workup

  1. temperaturerefluxed for 1 hour
  2. customthe THF was evaporated off
  3. customthe residue was then purified on silica gel (90/10 CH2Cl2/methanol)

Sources & evidence

ORD record
ord-70ff02f2437042409b90c481b06fcd0b
Source dataset
uspto-grants-2012_12
Patent number
US08338599B2

Reaction notes

Loading…