4-Toluenesulfonyl chloride → 3-Bromo-1-(4-methylbenzene-1-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 877915Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877915
[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[Li]CCCC.[S:16](Cl)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17]>C1COCC1>[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:16]([C:19]2[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:3]=1

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 55236593-Bromo-1H-pyrrolo[2,3-b]pyridineHCID 178418339Butyllithium

Produkt 1

HCID 216691553-Bromo-1-(4-methylbenzene-1-sulfonyl)-1H-pyrrolo[2,3-b]pyridineAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

3 g (0.015 mol) of 2 in 20 mL of anhydrous THF was cooled to −78° C. and n-BuLi 2.5 M in hexanes (6.7 mL, 0.167 mol) was added dropwise. After 15 minutes of stirring, tosyl chloride in 5 mL of THF was added dropwise. The cooling bath was removed and the reaction mixture stirred at rt for 1 h. Extracted with ether and the organic phase washed with brine, dried with magnesium sulfate and concentrated in vacuo to give a white solid that was passed through a pad of silica (70% EtOAc; 30% Hexanes) to give 4.65 g (84%) of 3. 1H NMR CDCl3 8.4 (s, 1H), 8.1 (d, 2H), 7.8 (s, 2H), 7.2 (m, 3H), 2.3 (s, 3H).

Aufarbeitung

  1. customThe cooling bath was removed
  2. stirringthe reaction mixture stirred at rt for 1 h
  3. extractionExtracted with ether
  4. washthe organic phase washed with brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a white solid

Quellen und Nachweise

ORD-Eintrag
ord-44d8aa56e0cf478aaafba326ae0fc7e7
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987454B2

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