Tetrabutylammonium Fluoride → 8-chloro-5-ethynyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1400616Notes

Reaction equation

HRID 1400616 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:11]#[C:12][Si](C(C)C)(C(C)C)C(C)C)[C:6]3[CH2:23][CH2:24][N:25]([CH3:27])[CH2:26][C:5]=3[C:4]=2[CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:11]#[CH:12])[C:6]3[CH2:23][CH2:24][N:25]([CH3:27])[CH2:26][C:5]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59455109HCID 59455109, compound

Product 1

HCID 594552058-chloro-5-ethynyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoleYield 143%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled solution of 8-chloro-2-methyl-5-((triisopropylsilyl)ethynyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (8.0 g, 0.02 mol) in THF (100 mL) was added tetrabutylammonium fluoride solution (1.0M in THF, 40 mL, 0.04 mol) at 0° C. over 15 min. The reaction mixture was stirred for 1 h at 0° C., after completion of reaction (monitored by TLC), 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 (7.0 g).

Workup

  1. customafter completion of reaction (monitored by TLC)
  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-885a8655a9664ba09c5c89c8abd3c8da
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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