Hydrochloric Acid → methyl 6-iodo-4H-furo[3,2-b]pyrrole-5-carboxylate

HRID 1363303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1363303
[O:1]1[C:8]2[CH:7]=[C:6]([C:9]([O:11][CH3:12])=[O:10])[NH:5][C:4]=2[CH:3]=[CH:2]1.[OH-].[K+].[I:15]I.Cl>CN(C=O)C.O>[I:15][C:7]1[C:8]2[O:1][CH:2]=[CH:3][C:4]=2[NH:5][C:6]=1[C:9]([O:11][CH3:12])=[O:10]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 14797Potassium HydroxideHCID 5082263methyl 4H-furo[3,2-b]pyrrole-5-carboxylate

Produkt 1

HCID 59648511methyl 6-iodo-4H-furo[3,2-b]pyrrole-5-carboxylateAusbeute 45,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

A mixture of methyl 4H-furo[3,2-b]pyrrole-5-carboxylate (5.00 g, 30.3 mmol) and KOH (3.40 g, 60.6 mmol) in DMF (100 mL) was cooled to −10° C. Iodine (7.31 g, 28.8 mmol) in DMF (40 mL) was charged via an addition funnel over 30 min. The resulting mixture was warmed to rt and stirred for additional 12 h. The reaction mixture was poured into water, adjusted with HCl (2 N) to pH 6-7, and extracted with EtOAc. The crude product was purified by flash chromatography (silica gel, 0 to 30% ethyl acetate in hexanes) to give a light tan solid methyl 6-iodo-4H-furo[3,2-b]pyrrole-5-carboxylate (3.85 g, 44% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 8.98 (br, s, 1H); 7.55 (d, J=2 Hz, 1H); 6.52 (d, J=2 Hz, 1H); 3.91 (s, 3H). MS (m/z 291).

Aufarbeitung

  1. temperatureThe resulting mixture was warmed to rt
  2. extractionextracted with EtOAc
  3. customThe crude product was purified by flash chromatography (silica gel, 0 to 30% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f7a3e93f2c2b4f05864f36ba15f1c333
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07884124B2

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