4-(5-Iodoindazole-1-yl)-benzoic acid → (4-(5-iodo-1H-indazol-1-yl)phenyl)methanol

HRID 13176

Reaktionsgleichung

Reaktionsgleichung von HRID 13176
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][CH:12]=1)[N:6]=[CH:5]2>C1COCC1>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:19]=[CH:18][C:14]([CH2:15][OH:16])=[CH:13][CH:12]=1)[N:6]=[CH:5]2

Komponenten

3

Edukt 1

HCID 593397454-(5-Iodoindazole-1-yl)-benzoic acid

Produkt 1

HCID 59339895(4-(5-iodo-1H-indazol-1-yl)phenyl)methanolAusbeute 71,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Crude 4-(5-iodo-1H-indazol-1-yl)benzoic acid (141c, 3.05 g, 8.4 mmol) was dissolved in THF (60 mL, dried over 4 Å MS) under argon atmosphere and cooled in an ice bath. Borane-THF complex (1M, 11 mL, 11 mmol) was added during 5 min. The ice bath was then removed and the mixture was allowed to reach r.t. and was finally heated at reflux for 40 min. The reaction mixture was then cooled to r.t. and sat. aqueous NH4Cl (25 mL) was added. After being diluted with EtOAc the reaction mixture was extracted trice with water and finally with brine and evaporated. The residue was subjected to chromatography (SiO2, 10-80% EtOAc in Heptane) to give (4-(5-iodo-1H-indazol-1-yl)phenyl)methanol (2.1 g, 71%).

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. additionBorane-THF complex (1M, 11 mL, 11 mmol) was added during 5 min
  3. customThe ice bath was then removed
  4. customto reach r.t.
  5. temperaturewas finally heated
  6. temperatureat reflux for 40 min
  7. additionsat. aqueous NH4Cl (25 mL) was added
  8. additionAfter being diluted with EtOAc the reaction mixture
  9. extractionwas extracted trice with water
  10. customfinally with brine and evaporated

Quellen und Nachweise

ORD-Eintrag
ord-e546c8b62cda4dbf9a7ab1ccf27aae67
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728030B2

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