Tetrabutylammonium Fluoride → HCID 89812915, compound

HRID 717113Notes

Reaction equation

HRID 717113 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[NH:22][C:23](=[O:37])[C:24]4[C:29]([CH:30]=3)=[C:28]([C:31]#[C:32][Si](C)(C)C)[CH:27]=[CH:26][CH:25]=4)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[NH:22][C:23](=[O:37])[C:24]4[C:29]([CH:30]=3)=[C:28]([C:31]#[CH:32])[CH:27]=[CH:26][CH:25]=4)=[CH:17][CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 89812812HCID 89812812, compound

Product 1

HCID 89812915HCID 89812915, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-[4-(1-oxo-5-trimethylsilanylethynyl-1,2-dihydroisoquinolin-3-yl)benzyl]piperazine-1-carboxylic acid tert-butyl ester compound (70.0 mg, 0.136 mmol) in THF (5 mL) was added TBAF (1M in THF, 272 μL, 0.272 mmol). The resulting reaction mixture was stirred at RT for 2 h and then quenched by the addition of water (20 mL). The mixture was extracted with EtOAc (3×20 mL) and the combined organic layer was washed with brine (50 mL), dried over Na2SO4, filtered and concentrated in vacuo to obtain 4-[4-(5-ethynyl-1-oxo-1,2-dihydroisoquinolin-3-yl)benzyl]piperazine-1-carboxylic acid tert-butyl ester (60.3 mg, 100%) as an orange solid. The crude compound was used for the next step without further purification.

Workup

  1. customThe resulting reaction mixture
  2. customquenched by the addition of water (20 mL)
  3. extractionThe mixture was extracted with EtOAc (3×20 mL)
  4. washthe combined organic layer was washed with brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46cdfc7b73a548159b4c5b67bc50ad69
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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