Tetrabutylammonium Fluoride → HCID 71503452, compound

HRID 574212Notes

Reaction equation

HRID 574212 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]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 867295996-Cyclopropyl-2-(5-(1,1,1-trifluoro-2-(triisopropylsilyloxy)propan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)pyridin-3-amine

Product 1

HCID 71503452HCID 71503452, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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;

Workup

  1. filtrationfiltered through Celite® (filter material)
  2. washThe mixture was washed through with THF (10 ml)
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give an orange oil
  5. customPurification of the oil by chromatography on silica eluting with 0-40% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-4297cf5f55474a96bb6fb412f4e2718f
Source dataset
uspto-grants-2015_05
Patent number
US09034879B2

Reaction notes

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