Triethylamine → 5-Nitro-3-(trimethylsilylethynyl)-indazole-1 carboxylic acid tert-butyl ester

HRID 1823916Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1823916
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-:19])=[O:18])=[CH:14][CH:15]=2)[C:10](Br)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:28][Si:29]([C:32]#[CH:33])([CH3:31])[CH3:30]>CN(C=O)C.[Cu](I)I>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-:19])=[O:18])=[CH:14][CH:15]=2)[C:10]([C:33]#[C:32][Si:29]([CH3:31])([CH3:30])[CH3:28])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 8471Triethylamine2×HCID 66111TrimethylsilylacetyleneHCID 222608361-Boc-3-bromo-5-nitro-1H-indazole

Produkt 1

HCID 600647035-Nitro-3-(trimethylsilylethynyl)-indazole-1 carboxylic acid tert-butyl esterAusbeute 45,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

3-Bromo 5-nitro-indazole-1-carboxylic acid tert-butyl ester (2 g, 5.8 mmol) was dissolved in dry DMF (30 mL) under nitrogen and triethylamine (1.6 mL, 1.6 mmol) added. Copper iodide (20 mg, 0.12 mmol), trimethylsilylacetylene (2.5 mL, 17.4 mmol) palladium bis-triphenylphosphine dichloride (84 mg, 0.12 mmol) and a further 1.6 mL of triethylamine were added and the mixture heated at 50° C. overnight. The reaction mixture was allowed to cool to room temperature and concentrated. The residue was taken up in EtOAc and filtered through a plug of Celite®. The filtrate was washed with saturated ammonium chloride solution and dried over sodium sulfate then concentrated to a black foam. Purification by chromatography (silica, 1:1 petrol-EtOAc) gave the title compound as a black solid (940 mg, 45%); MS (ES+) m/e=360.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. concentrationconcentrated
  3. filtrationfiltered through a plug of Celite®
  4. washThe filtrate was washed with saturated ammonium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationthen concentrated to a black foam
  7. customPurification by chromatography (silica, 1:1 petrol-EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-55b7a0b7624949af99d16aead348262a
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07041687B2

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