Tetrabutylammonium Fluoride → HCID 70664629, compound

HRID 1403477Notes

Reaction equation

HRID 1403477 reaction equation
[CH3:1][N:2]([CH:31]([CH3:33])[CH3:32])[C:3]1[C:4]([C:16]2[CH:20]=[CH:19][N:18]([Si](C(C)C)(C(C)C)C(C)C)[CH:17]=2)=[N:5][C:6]2[C:11]([N:12]=1)=[CH:10][C:9]([C:13]([O-:15])=[O:14])=[CH:8][CH:7]=2.[CH3:34]CCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:1][N:2]([CH:31]([CH3:33])[CH3:32])[C:3]1[C:4]([C:16]2[CH:20]=[CH:19][NH:18][CH:17]=2)=[N:5][C:6]2[C:11]([N:12]=1)=[CH:10][C:9]([C:13]([O:15][CH3:34])=[O:14])=[CH:8][CH:7]=2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86670570HCID 86670570, compound

Product 1

HCID 70664629HCID 70664629, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[methyl(propan-2-yl)amino]-2-[1-[tris(propan-2-yl)silyl]-1H-pyrrol-3-yl]quinoxaline-6-carboxylate (130 mg, 0.27 mmol) in THF (10 mL) was added TBAF (71 mg, 0.27 mmol) with stirring for 10 min at room temperature. The resulting mixture was concentrated under vacuum, diluted with water (30 mL), and extracted with ethyl acetate (2×30 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and the solids were collected via filtration. The resulting mixture was concentrated under vacuum to give methyl 3-[methyl(propan-2-yl)amino]-2-(1H-pyrrol-3-yl)quinoxaline-6-carboxylate (70 mg, 80%) as yellow oil.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. additiondiluted with water (30 mL)
  3. extractionextracted with ethyl acetate (2×30 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationthe solids were collected via filtration
  6. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-ddbdf1f886e14f51ad14ab7687bdaa30
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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