Tetrabutylammonium Fluoride → HCID 71503452, compound
Reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[O:11][C:12]([C:15]([O:21][Si](C(C)C)(C(C)C)C(C)C)([CH3:20])[C:16]([F:19])([F:18])[F:17])=[N:13][N:14]=3)[C:7]([NH2:32])=[CH:6][C:5]=2[C:33]([F:36])([F:35])[F:34])[CH2:3][CH2:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[NH2:32][C:7]1[C:8]([C:10]2[O:11][C:12]([C:15]([OH:21])([CH3:20])[C:16]([F:19])([F:18])[F:17])=[N:13][N:14]=2)=[N:9][C:4]([CH:1]2[CH2:3][CH2:2]2)=[C:5]([C:33]([F:34])([F:36])[F:35])[CH:6]=1Participants
4
Procedure
A solution of 6-cyclopropyl-2-(5-(1,1,1-trifluoro-2-(triisopropylsilyloxy)propan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyridin-3-amine (step 4) (200 mg, 0.371 mmol) in dry THF (10 ml) was treated with silica supported tetra-n-butylammonium fluoride (500 mg, 0.750 mmol). The resulting red suspension was stirred at RT for 5 minutes and filtered through Celite® (filter material). The mixture was washed through with THF (10 ml) and the filtrate was concentrated in vacuo to give an orange oil. Purification of the oil by chromatography on silica eluting with 0-40% EtOAc in iso-hexane afforded the title compound;