Iodine → HCID 178506359, Verbindung

HRID 246364Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 246364
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2C(O)=O.C(=O)(O)[O-].[Na+].[I-:23].[Na+].II>ClC(Cl)C.O.ClCCl>[I:23][C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([O:3][C:2]([F:17])([F:16])[F:1])[CH:5]=2)[NH:9][N:8]=1

Komponenten

8

Edukt 4

HCID 807IodineHCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 299215515-(trifluoromethoxy)-1H-indazole-3-carboxylic acid

Produkt 1

HCID 178506359HCID 178506359, VerbindungAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 63651,1-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of 5-(trifluoromethoxy)-1H-indazole-3-carboxylic acid (0.2 g, 813 μmol), and sodium bicarbonate (225 mg, 104 μL, 2.68 mmol) in dichloroethane (2 mL) and water (2.00 mL) were added in one portion sodium iodide (317 mg, 2.11 mmol) and iodine (268 mg, 1.06 mmol) and the mixture heated at 100° C. (oil bath temperature) with vigorous stirring for 45 minutes. After cooling to 25° C. the mixture was diluted with dichloromethane, then washed with 10% Na2S2O3 and saturated NaHCO3. The organics were dried (MgSO4) and concentrated to an off-white solid which was dissolved in dichloromethane, cyclohexane added to promote solid formation, and allowed to stand. The solid was separated by filtration and dried to give 3-iodo-5-(trifluoromethoxy)-1H-indazole (178 mg, 543 μmol, 67%) as white needles. MS (M−H)−=326.8; 1H NMR (CDCl3) δ: 7.51 (d, J=9.1 Hz, 1H), 7.40 (s, 1H), 7.32-7.38 (m, 1H).

Aufarbeitung

  1. temperatureAfter cooling to 25° C. the mixture
  2. washwashed with 10% Na2S2O3 and saturated NaHCO3
  3. dry with materialThe organics were dried (MgSO4)
  4. concentrationconcentrated to an off-white solid which
  5. dissolutionwas dissolved in dichloromethane
  6. additioncyclohexane added
  7. customThe solid was separated by filtration
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2f76e282eb2749f5b33445bff6d3df8c
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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