O-Phenylenediamine → 3-(1H-Benzo[d]imidazol-2-yl)-5-bromo-1H-indazole

HRID 1047523Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1047523
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[CH:11]=O.[C:13]1([NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:19].S(=O)(O)[O-].[Na+]>C1COCC1.Cl.C(OCC)(=O)C>[NH:19]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:20]=[C:11]1[C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=2)[NH:7][N:6]=1

Komponenten

7

Edukt 3

HCID 7243O-PhenylenediamineHCID 23665763Sodium BisulfiteHCID 178520023HCID 178520023, Verbindung

Produkt 1

HCID 1358201453-(1H-Benzo[d]imidazol-2-yl)-5-bromo-1H-indazoleAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-Bromo-1H-indazole-3-carbaldehyde (50 mg, 0.222 mmol) and o-phenylene diamine (24 mg, 0.222 mmol) were dissolved in dry THF (10 mL). One drop of 2N HCl was added. The solution was heated at a gentle reflux for 30 min and then 1N sodium bisulfite (1 mL) was added. After overnight at reflux, the solution was cooled to room temperature, and then diluted with ethyl acetate (30 mL). The mixture was washed with water and brine, dried over Na2SO4, and concentrated. Purification by flash chromatography (20% ethyl acetate/hexane) afforded the title compound as a pale yellow solid in a 50% yield. 1H NMR (400 MHz, CDCl3): δ 8.73 (d, 1H, J=1.2 Hz), 7.80 (m, 1H), 7.48-7.45 (m, 2H), 7.37 (d, 1H, J=8.8 Hz), 7.23 (m, 2H); ESI-MS [M+H]+: 313.0.

Aufarbeitung

  1. temperatureThe solution was heated at
  2. temperaturea gentle reflux for 30 min
  3. temperatureAfter overnight at reflux
  4. washThe mixture was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by flash chromatography (20% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0a5b981be7474585bf1659ce08bf6ab9
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569511B2

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