Hydrochloric Acid → ethyl 4-iodo-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

HRID 1752644Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1752644
O[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[N:14]([CH3:17])[CH:15]=[CH:16][C:3]=12.N1C=CC=CC=1.O(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.[Na+].[I-:40].Cl.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(#N)C.C(OCC)(=O)C>[I:40][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[N:14]([CH3:17])[CH:15]=[CH:16][C:3]=12

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 5238Sodium IodideHCID 24477Sodium ThiosulfateHCID 67749Trifluoromethanesulfonic anhydrideHCID 178469181HCID 178469181, Verbindung

Produkt 1

HCID 89923718ethyl 4-iodo-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A 0° C. solution of ethyl 4-hydroxy-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (10.0 g, 42.7 mmol) in acetonitrile (200 mL) and pyridine (4.13 mL, 51.2 mmol) was treated dropwise with Tf2O (8.65 mL, 51.2 mmol). After 1 h, the reaction mixture was treated with NaI (19.20 g, 128 mmol) followed by dropwise addition of 3M HCl (17.08 mL, 51.2 mmol) and warmed to 70° C. After 3 h, the reaction mixture was cooled to ambient temperature and added to a sat. aq. solution of Na2S2O3. After stirring for 15 min, ethyl acetate was added and the layers partitioned. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to afford ethyl 4-iodo-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (14.7 g).

Aufarbeitung

  1. waitAfter 3 h
  2. temperaturethe reaction mixture was cooled to ambient temperature
  3. customthe layers partitioned
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e24b3608d123461080f3bb1f709871d2
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09163023B2

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