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Sodium Iodide → 3-(2-Fluoro-4-iodo-phenylamino)-thieno[2,3-c]pyridine-2-carboxylic acid ethyl ester

HRID 1366783
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1366783
[CH2:1]([O:3][C:4]([C:6]1[S:14][C:9]2=[CH:10][N:11]=[CH:12][CH:13]=[C:8]2[C:7]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19](Br)=[CH:18][C:17]=1[F:23])=[O:5])[CH3:2].[I-:24].[Na+].CN[C@@H]1CCCC[C@H]1NC>O1CCOCC1.[Cu]I>[CH2:1]([O:3][C:4]([C:6]1[S:14][C:9]2=[CH:10][N:11]=[CH:12][CH:13]=[C:8]2[C:7]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([I:24])=[CH:18][C:17]=1[F:23])=[O:5])[CH3:2]
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Komponenten

6

Edukt 3

HCID 5238Sodium IodideHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine2×HCID 59703899Ethyl 3-(4-bromo-2-fluoro-phenylamino)-thieno[2,3-c]pyridine-2-carboxylate

Produkt 1

HCID 597039023-(2-Fluoro-4-iodo-phenylamino)-thieno[2,3-c]pyridine-2-carboxylic acid ethyl esterAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
2×
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A mixture of 3-(4-bromo-2-fluoro-phenylamino)-thieno[2,3-c]pyridine-2-carboxylic acid ethyl ester (288 mg, 0.73 mmol), copper (1) iodide (7 mg, 0.036 mmol), sodium iodide (219 mg, 1.46 mmol) and trans-N,N′-dimethyl-1,2-cyclohexane diamine (10.4 mg, 0.073 mmol) in 1,4-dioxane (1.0 ml) was heated at 105° C. for 24 hours under an argon atmosphere. Copper (I) iodide (7 mg, 0.036 mmol) and trans-N,N′-dimethyl-1,2-cyclohexane diamine (10.4 mg, 0.073 mmol) were added and heating continued for a further 24 hours. The reaction was cooled to room temperature and the mixture was partitioned between DCM (30 ml), concentrated aqueous ammonia (2 ml) and water (13 ml). The organic layer was isolated, dried over sodium sulphate, filtered and evaporated then the residue was purified by flash chromatography (Si-SPE, DCM) to afford the title compound as a yellow solid (275 mg, 85%). LCMS (method B): RT=4.23 min, M+H+=443.

Aufarbeitung

  1. temperatureheating
  2. temperatureThe reaction was cooled to room temperature
  3. customthe mixture was partitioned between DCM (30 ml), concentrated aqueous ammonia (2 ml) and water (13 ml)
  4. customThe organic layer was isolated
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customthe residue was purified by flash chromatography (Si-SPE, DCM)

Quellen und Nachweise

ORD-Eintrag
ord-aff052e8af3f419cba5efd150af3d1ae
Quelldatensatz
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07893085B2

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