Acetic Acid → [1-(3,5-Bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazol-4-yl]-(3-phenyl-3H-[1,2,3]triazol-4-yl)-methanone

HRID 349286Notes

Reaction equation

HRID 349286 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]1[CH:4]=[C:5]([CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([C:18]([C:20]2[N:21]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:22]=[N:23][C:24]=2[Si](C)(C)C)=[O:19])[N:9]=[N:8]1.[F-].C([NH3+])(C)(C)C.C(O)(=O)C>C1COCC1>[F:43][C:2]([F:1])([F:42])[C:3]1[CH:4]=[C:5]([CH:35]=[C:36]([C:38]([F:39])([F:41])[F:40])[CH:37]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([C:18]([C:20]2[N:21]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:22]=[N:23][CH:24]=2)=[O:19])[N:9]=[N:8]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 21866379t-Butylammonium fluorideHCID 86601239[1-(3,5-Bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazol-4-yl]-(3-phenyl-5-trimethylsilanyl-3H-[1,2,3]triazol-4-yl)-methanone

Product 1

HCID 58804034[1-(3,5-Bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazol-4-yl]-(3-phenyl-3H-[1,2,3]triazol-4-yl)-methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of [1-(3,5-Bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazol-4-yl]-(3-phenyl-5-trimethylsilanyl-3H-[1,2,3]triazol-4-yl)-methanone (0.050 g, 0.08 mmol) in THF (2 mL) add t-butyl ammonium flouride (1 M soln. in THF, 1.2 mL, 1.2 mmol) and acetic acid (120 μL, 2.0 mmol) and heat at 65° C. After 72 h., remove from heat, and quench with sat. aq. NH4C1 and H2O. Extract with EtOAc, dry over MgSO4, filter, and purify by flash chromatography (EtOAc/Hexane 0%–50%) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 8.88 (s, 1H), 7.75 (s, 1H), 7.57–7.29 (m, 10H), 7.09 (m, 2H), 5.50 (s, 2H).

Workup

  1. customremove
  2. temperaturefrom heat
  3. customquench with sat. aq. NH4C1 and H2O
  4. extractionExtract with EtOAc
  5. dry with materialdry over MgSO4
  6. filtrationfilter
  7. custompurify by flash chromatography (EtOAc/Hexane 0%–50%)

Sources & evidence

ORD record
ord-6a3f7472d5324174ba00cac6ebc6f7c2
Source dataset
uspto-grants-2007_02
Patent number
US07179804B2

Reaction notes

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