Tetrabutylammonium Fluoride → HCID 19593035, compound

HRID 613479Notes

Reaction equation

HRID 613479 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13]([C:17]#[C:18][Si](C)(C)C)=[CH:12]2)=[O:5].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.ClCCl>[Cl:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13]([C:17]#[CH:18])=[CH:12]2)=[O:5]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 19592862HCID 19592862, compound

Product 1

HCID 19593035HCID 19593035, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 8-(2,6-dichlorobenzoylamino)-3-(trimethylsilylethynyl)quinoline (150 mg) in tetrahydrofuran (3 ml) was added 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.04 ml) under ice-cooling, and the mixture was stirred for 2 hours at the same temperature. The mixture was diluted with dichloromethane, washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate:n-hexane, 1:4, v/v) to give 8-(2,6-dichlorobenzoylamino)-3-ethynylquinoline (111 mg).

Workup

  1. temperaturecooling
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:n-hexane, 1:4, v/v)

Sources & evidence

ORD record
ord-d25144b414e74da6991ed254f8447691
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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