Pyridine → HCID 18973928, compound

HRID 2395026Notes

Reaction equation

HRID 2395026 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH2:14]([O:21][C:22]1[CH:39]=[CH:38][CH:37]=[CH:36][C:23]=1[CH2:24][CH2:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH2:32])=O)=[CH:28][C:27]=1[Br:35])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.N1C=CC=CC=1>C1COCC1.C(OCC)(=O)C>[CH2:14]([O:21][C:22]1[CH:39]=[CH:38][CH:37]=[CH:36][C:23]=1[CH2:24][CH2:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]#[N:32])=[CH:28][C:27]=1[Br:35])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 18974069HCID 18974069, compound

Product 1

HCID 18973928HCID 18973928, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trifluoroacetic anhydride (0.75 ml) was added to a mixture of 4-[2-benzyloxyphenethyl]-3-bromobenzamide (1.46 g) and pyridine (0.86 ml) in THF at -20° C. The mixture was stirred at ambient temperature for 18 hours, diluted with ethyl acetate and washed with water, dried (MgSO4), filtered and evaporated to dryness. The resulting residue was purified by MPLC on silica gel, eluting with CH2Cl2 to give 4-[2-benzyloxyphenethyl]-3-bromobenzonitrile as a white solid (1.34 g).

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe resulting residue was purified by MPLC on silica gel
  6. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-2e891898aee641aab7a1cde24e80181e
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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