N-Iodosuccinimide → 3-iodo-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine

HRID 1253455Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1253455
[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:15]=[CH:16][CH:17]=2)[CH:6]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[CH:8]=1.[I:18]N1C(=O)CCC1=O>C(#N)C.ClCCl>[I:18][C:17]1[CH:16]=[N:15][N:5]2[CH:6]=[C:7]([C:9]3[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=3)[CH:8]=[C:3]([O:2][CH3:1])[C:4]=12

Komponenten

5

Edukt 2

HCID 120273N-IodosuccinimideHCID 58404846HCID 58404846, Verbindung

Produkt 1

HCID 448167683-iodo-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine (486 mg, 2.13 mmol) was suspended in acetonitrile (30 ml). N-iodosuccinimide (958 mg, 4.26 mmol) was added and the mixture was allowed to stir for 1 h. The reaction mixture was diluted in dichloromethane, washed with water, 1N aqueous sodium hydroxide and brine. The combined organic layers were dried over sodium sulfate, filtered, and concentrated to afford 3-iodo-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine as a tan solid. 1H NMR (500 MHz, DMSO-d6) δ 8.67 (s, 1H); 8.28 (s, 1H); 8.01 (s, 1H); 7.92 (1, 1H); 6.89 (s, 1H); 3.96 (s, 3H); 3.85 (s, 3H). LRMS (ESI) calculated for C12H12IN4O [M+H]+, 355.0; found 354.9.

Aufarbeitung

  1. washwashed with water, 1N aqueous sodium hydroxide and brine
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7f4901e0bcb648b7bc9e5b4559f2495f
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455477B2

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