Tetrabutylammonium Fluoride → 4-Chloro-2-methyl-7-azaindole

HRID 347560Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 347560
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8](COCC[Si](C)(C)C)[C:9]([CH3:11])=[CH:10][C:3]=12.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([CH3:11])=[CH:10][C:3]=12

Komponenten

3

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 210816744-Chloro-2-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 210816754-Chloro-2-methyl-7-azaindoleAusbeute 60,6 %

Versuchsvorschrift

A mixture of 4-chloro-2-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo-[2,3-b]pyridine (296.5 mg, 1 mmol) and TBAF (5 mL, 1 M in THF, Aldrich) was refluxed overnight. The THF was removed under reduced pressure and the residue was diluted with water (5 mL). The precipitate that formed was collected, washed with water and dried (MgSO4) to afford the title compound (101 mg, 60%). 1H NMR (CD3OD) δ 7.99 (d, 1H, J=5.5 Hz), 7.06 (d, 1H, J=5.5 Hz), 6.23 (s, 1H), 2.46 (s, 3H); MS(ESI+) m/z 167 and 169 (M+H, 1 Cl)+.

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. customThe THF was removed under reduced pressure
  3. additionthe residue was diluted with water (5 mL)
  4. customThe precipitate that formed
  5. customwas collected
  6. washwashed with water
  7. dry with materialdried (MgSO4)

Quellen und Nachweise

ORD-Eintrag
ord-f61b5f9916b1442abd59ad92987b11ad
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173031B2

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