Tetrabutylammonium Fluoride → 5-Ethynyl-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1401682Notes

Reaction equation

HRID 1401682 reaction equation
[CH3:1][N:2]1[CH2:27][CH2:26][C:5]2[N:6]([C:14]#[C:15][Si](C(C)C)(C(C)C)C(C)C)[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O>[C:14]([N:6]1[C:7]2[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=2[C:4]2[CH2:3][N:2]([CH3:1])[CH2:27][CH2:26][C:5]1=2)#[CH:15]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59454929HCID 59454929, compound

Product 1

HCID 594550005-Ethynyl-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoleYield 177.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled solution of 2,8-dimethyl-5-((triisopropylsilyl)ethynyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (10 g, 0.0236 mol) in THF (100 mL) was added tetrabutylammonium fluoride solution (1.0M in THF, 49 mL, 0.0526 mol) at 0° C. over 15 min. The reaction mixture was stirred for 1 h at 0° C., and the reaction monitored by TLC. After completion of reaction, the mixture was diluted with water (100 mL) and extracted with EtOAc (3×100 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduce pressure to obtain product as a brown colored oil (9.4 g).

Workup

  1. customAfter completion of reaction
  2. extractionextracted with EtOAc (3×100 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-28629f3e3ca8490c8af9facc58cebc8e
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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