Iodine → 3-Iodo-5-phenylsulfanyl-1H-pyrrolo[2,3-b]pyridine

HRID 1991094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1991094
[C:1]1([S:7][C:8]2[CH:9]=[C:10]3[CH:16]=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[I:19]I.[O-]S([O-])(=S)=O.[Na+].[Na+]>CN(C=O)C.O>[I:19][C:16]1[C:10]2[C:11](=[N:12][CH:13]=[C:8]([S:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:9]=2)[NH:14][CH:15]=1

Komponenten

7

Edukt 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 24477Sodium ThiosulfateHCID 591287095-Phenylsulfanyl-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 591287053-Iodo-5-phenylsulfanyl-1H-pyrrolo[2,3-b]pyridineAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2 (135 mg, 0.60 mmol) in DMF (1.5 mL) was added solid KOH (124 mg, 2.21 mmol) and the reaction mixture stirred for 20 min. Iodine (167 mg, 0.66 mmol) was then added and the stirring continued for 40 min. A mixture of water (8.8 mL) and sat. aq. Na2S2O3 (1.3 mL) was added rapidly, and the resulting solid filtered off, washed with water (2×) and dried in vacuum to give iodide 3 as a creamy solid (205 mg, 98%); 1H NMR (400 MHz, CDCl3+2 drops CD3OD) δ 7.10-7.30 (m, 5H), 7.45 (s, 1H), 7.94 (d, J=2.0 Hz, 1H), 8.35 (d, J=1.9 Hz, 1H).

Aufarbeitung

  1. waitthe stirring continued for 40 min
  2. additionwas added rapidly
  3. filtrationthe resulting solid filtered off
  4. washwashed with water (2×)
  5. customdried in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-333e844165204f2bb43227c41999f2f3
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07645769B2

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