7-Nitroindazole → tert-Butyl 7-nitro-1H-indazole-1-carboxylate

HRID 482343

Reaktionsgleichung

Reaktionsgleichung von HRID 482343
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][N:10]=[CH:9]2)([O-:3])=[O:2].[C:13](=O)([O:19]C(C)(C)C)[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(#N)C>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[N:11]([C:13]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:19])[N:10]=[CH:9]2)([O-:3])=[O:2]

Komponenten

6

Edukt 3

HCID 18937-NitroindazoleHCID 8471TriethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Produkt 1

HCID 15606021tert-Butyl 7-nitro-1H-indazole-1-carboxylateAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 7-nitro-1H-indazole (2.81 g, 17.23 mmol), di-tertbutyl carbonate (7.52 g, 34.5 mmol), triethylamine (4.81 mL, 34.5 mmol) and 4-dimethylamino-pyridine (2.11 g, 17.2 mmol) in anhydrous acetonitrile (100 mL) is stirred under nitrogen at ambient temperature for approximately 3 hrs. After removing the solvent in vacuo, the residue is partitioned between ethyl acetate and aqueous sodium hydrogen sulfate (1N). The organic layer is separated, washed with saturated aqueous brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The crude product is purified by chromatography on flash grade silica gel using DCM. Fractions containing the product are combined, concentrated in vacuo to a solid and dried under high vacuum to provide the title compound as a yellow solid (2.674 g, 10.16 mmol). 1H NMR (300 MHz, d6-DMSO) δ=1.55 (s, 9H); 7.58 (t, J=8.0 Hz, 1H); 8.20 (d, J=7.4 Hz, 1H); 8.30 (d, J=7.7 Hz, 1H); 8.67 (s, 1H), TLC: Rf =0.5 (DCM).

Aufarbeitung

  1. customAfter removing the solvent in vacuo
  2. customthe residue is partitioned between ethyl acetate and aqueous sodium hydrogen sulfate (1N)
  3. customThe organic layer is separated
  4. washwashed with saturated aqueous brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified by chromatography on flash grade silica gel
  9. additionFractions containing the product
  10. concentrationconcentrated in vacuo to a solid
  11. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b6abbb564f7b405db91470f74f1214ec
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05795887

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