TBAF tetrahydrofuran → HCID 18548957, compound

HRID 1266308Notes

Reaction equation

HRID 1266308 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>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 11078149TBAF tetrahydrofuranHCID 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/tetrahydrofuran. 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-9f0b9c4eef764b91ad6fd5b9610342db
Source dataset
uspto-grants-2003_04
Patent number
US06548496B2

Reaction notes

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