Potassium Carbonate → 2-(5-(3,4-bis(benzyloxy)-5-nitrophenyl)-2H-tetrazol-2-yl)-5-(trifluoromethyl)pyridine

HRID 42664Notes

Reaction equation

HRID 42664 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[CH2:12]([O:19][C:20]1[CH:21]=[C:22]([C:37]2[N:38]=[N:39][NH:40][N:41]=2)[CH:23]=[C:24]([N+:34]([O-:36])=[O:35])[C:25]=1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.ClCCl>[CH2:12]([O:19][C:20]1[CH:21]=[C:22]([C:37]2[N:38]=[N:39][N:40]([C:2]3[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=3)[N:41]=2)[CH:23]=[C:24]([N+:34]([O-:36])=[O:35])[C:25]=1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 670370545-[3,4-Bis(benzyloxy)-5-nitrophenyl]-2H-tetrazole

Product 1

HCID 687056332-(5-(3,4-bis(benzyloxy)-5-nitrophenyl)-2H-tetrazol-2-yl)-5-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

2-chloro-5-(trifluoromethyl)pyridine (0.181 g, 1.00 mmol) was added to a stirred suspension of 5-(3,4-bis-benzyloxy-5-nitro-phenyl)-2H-tetrazole (0.4 g, 1.00 mmol) and potassium carbonate (0.14 g, 1 mmol) in acetonitrile (10 mL). The reaction mixture was stirred at room temperature till completion, then diluted with dichloromethane and washed with water. The organic phase was separated, dried over anhydrous magnesium sulphate, filtered and evaporated to dryness to leave a crude residue that was recrystallised from a dichloro-methane/isopropanol mixture to afford 2-(5-(3,4-bis(benzyloxy)-5-nitrophenyl)-2H-tetrazol-2-yl)-5-(trifluoromethyl)pyridine, 0.389 g (71%).

Workup

  1. washwashed with water
  2. customThe organic phase was separated
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customto leave a crude residue that
  7. customwas recrystallised from a dichloro-methane/isopropanol mixture

Sources & evidence

ORD record
ord-59d3bf07cc534abdaef6b578d59566c3
Source dataset
uspto-grants-2013_09
Patent number
US08536203B2

Reaction notes

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