Triphenylphosphine → 2-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanamine

HRID 1777584Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1777584
[N:1]([CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([Cl:15])[CH:13]=2)[NH:8][C:7]=1[Si:16]([CH2:21][CH3:22])([CH2:19][CH3:20])[CH2:17][CH3:18])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CO>[Cl:15][C:12]1[CH:13]=[C:14]2[C:6]([CH2:5][CH2:4][NH2:1])=[C:7]([Si:16]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:21][CH3:22])[NH:8][C:9]2=[N:10][CH:11]=1

Komponenten

4

Edukt 2

HCID 11776TriphenylphosphineHCID 866638403-(2-azidoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 668320582-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanamineAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 3-(2-azidoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine (0.900 g; 2.68 mmol) and triphenylphosphine 1.05 g; 4.02 mmol) in methanol (25 ml) was stirred at 80° C. for 1 hour and was concentrated under reduced pressure. The residue was dissolved in toluene (15 mL). Hydrochloric acid (2 mL) and water 15 mL were added. After separation of the two layers, the aqueous solution was extracted with toluene (3×15 mL) and was made alkaline by addition of an aqueous solution of sodium hydroxide 2N. The formed precipitate was filtered off. The filtrate was extracted with dichloromethane (5×15 mL). Combined dichloromethane extracts were dried over magnesium sulfate and was concentrated in vacuo to give 0.515 g (62%) of 2-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanamine as an oily residue.

Aufarbeitung

  1. concentrationwas concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in toluene (15 mL)
  3. additionHydrochloric acid (2 mL) and water 15 mL were added
  4. customAfter separation of the two layers
  5. extractionthe aqueous solution was extracted with toluene (3×15 mL)
  6. additionby addition of an aqueous solution of sodium hydroxide 2N
  7. filtrationThe formed precipitate was filtered off
  8. extractionThe filtrate was extracted with dichloromethane (5×15 mL)
  9. dry with materialCombined dichloromethane extracts were dried over magnesium sulfate
  10. concentrationwas concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-33231b1cc8a04e5c9766edeb1cc9ffd6
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266832B2

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