Iodine → HCID 178506566, Verbindung

HRID 245784

Reaktionsgleichung

Reaktionsgleichung von HRID 245784
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[I:10]I.[OH-].[K+]>CN(C=O)C>[I:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][N:2]=1

Komponenten

5

Edukt 3

HCID 807IodineHCID 92211H-IndazoleHCID 14797Potassium Hydroxide

Produkt 1

HCID 178506566HCID 178506566, VerbindungAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In a 50 mL round-bottomed flask, indazole (0.80 g, 6.8 mmol) was dissolved in DMF (14 mL). Iodine (3.4 g, 13.5 mmol) was added followed by potassium hydroxide (1.47 g, 26.2 mmol). The dark reaction mixture was stirred at room temperature for 1.25 h then was quenched with 10% aq NaHSO3 and extracted with diethyl ether (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated to give 1.65 g (95%) of 3-iodo-1H-indazole as a light yellow solid. 1H NMR (CDCl3, 300 MHz): δ (ppm) 10.56 (br. s, 1H), 7.47-7.57 (m, 3H), 7.23-7.30 (m, 1H).

Aufarbeitung

  1. customThe dark reaction mixture
  2. customthen was quenched with 10% aq NaHSO3
  3. extractionextracted with diethyl ether (2×)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialthen dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-95d34199a9a34642b649aa1b6be2f693
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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