Carbon tetrabromide → 3-(2-bromoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1777582

Reaktionsgleichung

Reaktionsgleichung von HRID 1777582
[C:1]([Br:5])(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:25][C:26]1[CH:27]=[C:28]2[C:34]([CH2:35]CO)=[C:33]([Si:38]([CH2:43][CH3:44])([CH2:41][CH3:42])[CH2:39][CH3:40])[NH:32][C:29]2=[N:30][CH:31]=1>C1COCC1>[Br:5][CH2:1][CH2:35][C:34]1[C:28]2[C:29](=[N:30][CH:31]=[C:26]([Cl:25])[CH:27]=2)[NH:32][C:33]=1[Si:38]([CH2:39][CH3:40])([CH2:43][CH3:44])[CH2:41][CH3:42]

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 110560231H-Pyrrolo[2,3-B]pyridine-3-ethanol, 5-chloro-2-(triethylsilyl)-

Produkt 1

HCID 668319713-(2-bromoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridineAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Carbon tetrabromide (3.27 g, 9.65 mmol) was added to a solution of triphenylphosphine (2.56 g; 9.65 mmol) in THF (30 mL). The mixture was stirred at room temperature for 30 minutes. To this green suspension was added a solution of 2-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol (2 g; 6.43 mmol) in THF (20 mL) and the resulting reaction mixture was stirred for 20 hours. The precipitate was eliminated by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (eluent 5 to 40% ethyl acetate in heptane) to give 1.08 g (45%) of 3-(2-bromoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine as a white solid.

Aufarbeitung

  1. customthe resulting reaction mixture
  2. stirringwas stirred for 20 hours
  3. filtrationThe precipitate was eliminated by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (eluent 5 to 40% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-d610fbfc39a14794985643cf250607fa
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266832B2

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