Tetrabutylammonium Fluoride → HCID 18548957, compound

HRID 276879Notes

Reaction equation

HRID 276879 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][N:15]=[C:16]([C:19]#[C:20][Si](C)(C)C)[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:25]#[N:26])[CH:5]=[CH:6][CH:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][N:15]=[C:16]([C:19]#[CH:20])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:25]#[N:26])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 18548976HCID 18548976, compound

Product 1

HCID 18548957HCID 18548957, compoundYield 45.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 800 mg of 4-(3-bromo-phenylamino)-6-trimethylsilanylethynyl-[1.7]naphthyridine-3-carbonitrile in 20 mL of tetrahydrofuran at 0° C. under an inert atmosphere was added 2.5 mL of 1 M tetrabutylammonium fluoride/tetrahydrofaran. After 1 hour at ambient temperature, the reaction was diluted with ethyl acetate and washed with brine. The organic layer was dried with sodium sulfate and evaporated. The product was purified by flash chromatography on silica gel to give 300 mg of 4-(3-bromo-phenylamino)-6-ethynyl-[1.7]naphthyridine-3-carbonitrile: melting point 224° C. (decomposed); mass spectrum (m/e): M+H 349.1, 351.1.

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. customevaporated
  4. customThe product was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-55445a3c802c4387b622d07c9fb587f7
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Reaction notes

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