Triethylamine → HCID 19093454, compound

HRID 487067Notes

Reaction equation

HRID 487067 reaction equation
C(N(CC)CC)C.[N:8](=[CH:10][C:11]1[CH:12]=[CH:13][C:14]2[C:15](=[O:25])[C:16]3[C:21]([C:22]=2[N:23]=1)=[CH:20][CH:19]=[C:18]([Br:24])[CH:17]=3)O.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O>C(Cl)Cl.C(OCC)(=O)C>[C:10]([C:11]1[CH:12]=[CH:13][C:14]2[C:15](=[O:25])[C:16]3[C:21]([C:22]=2[N:23]=1)=[CH:20][CH:19]=[C:18]([Br:24])[CH:17]=3)#[N:8]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 136378379HCID 136378379, compound

Product 1

HCID 19093454HCID 19093454, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2 Equivalents of triethylamine are added to a suspension of the oxime in dry methylene chloride at -78° under nitrogen. 1.1 equivalent of triflic anhydride are then added dropwise over 3 minutes. After stirring overnight, the reaction mixture is diluted with ethyl acetate and washed with 10% sodium bicarbonate solution. The organic phase is dried over anhydrous magnesium sulfate. Solvent removal provides the desired 3-cyano-7-bromo-4-aza-9-fluorenone.

Workup

  1. washwashed with 10% sodium bicarbonate solution
  2. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  3. customSolvent removal

Sources & evidence

ORD record
ord-6da7be05766a44a2a3c55f9ed82f3e8a
Source dataset
uspto-grants-1994_03
Patent number
US05294610

Reaction notes

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