Dichloromethane → 2-Chloro-7-iodo-5H-pyrrolo[2,3-b]pyrazine

HRID 390108Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 390108
[I:1]Cl.ClCCl.[Cl:6][C:7]1[N:8]=[C:9]2[CH:15]=[CH:14][NH:13][C:10]2=[N:11][CH:12]=1>N1C=CC=CC=1>[Cl:6][C:7]1[N:8]=[C:9]2[C:15]([I:1])=[CH:14][NH:13][C:10]2=[N:11][CH:12]=1

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 24640Iodine chlorideHCID 457896382-Chloro-5H-pyrrolo[2,3-B]pyrazine

Produkt 1

HCID 536276902-Chloro-7-iodo-5H-pyrrolo[2,3-b]pyrazineAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A 1 M solution of iodine monochloride in dichloromethane (9.84 mL, 9.84 mmol) was added dropwise to an ice-cold solution of 2-chloro-5H-pyrrolo[2,3-b]pyrazine (6.75 g, 11.07 mmol) in anhydrous pyridine (12 mL). The reaction mixture was stirred at 0° C. for 60 minutes, then concentrated. The residue was partitioned between ethyl acetate and brine. The organic phase was washed with brine and concentrated. The crude product was stirred with 15 mL of dichloromethane. The yellow solid material was collected by filtration, washed with dichloromethane and dried to give 2.86 g of the title product. Yield: 66%. MS (DCI+) m/z 280 (M+H)+.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and brine
  3. washThe organic phase was washed with brine
  4. concentrationconcentrated
  5. stirringThe crude product was stirred with 15 mL of dichloromethane
  6. filtrationThe yellow solid material was collected by filtration
  7. washwashed with dichloromethane
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-62318aa24301476089a5ce1db8fab759
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383624B2

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