Tetrahydrofuran → 1-(2-Aminopropyl)-1,4-dihydro-indeno[1,2-c]pyrazol-6-ol

HRID 1816464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1816464
C[O:2][C:3]1[CH:4]=[C:5]2[C:16](=[CH:17][CH:18]=1)[C:8]1[N:9]([CH2:12][CH:13]([NH2:15])[CH3:14])[N:10]=[CH:11][C:7]=1[CH2:6]2.[B-](Br)(Br)(Br)[S+](C)C.C1COCC1.C([O-])(O)=O.[Na+]>ClCCCl>[NH2:15][CH:13]([CH3:14])[CH2:12][N:9]1[C:8]2[C:16]3[C:5]([CH2:6][C:7]=2[CH:11]=[N:10]1)=[CH:4][C:3]([OH:2])=[CH:18][CH:17]=3

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 4181510Tribromoborane-methyl sulfideHCID 223383072-(6-Methoxy-4H-indeno[1,2-c]pyrazol-1-yl)-1-methylethylamine

Produkt 1

HCID 1354860361-(2-Aminopropyl)-1,4-dihydro-indeno[1,2-c]pyrazol-6-olAusbeute 13,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a solution of the product from Step D (0.56 g, 0.23 mmol) in 1,2-dichloroethane (10 mL) was added boron tribromide-methylsulfide complex in THF solution (1.0M, 0.5 mL, 0.5 mmol) and the solution heated to reflux for 16 h. The solution was allowed to cool, poured into aqueous NaHCO3, extracted with chloroform (2×20 mL), dried (Na2SO4) and concentrated. The crude product was purified by chromatography (silica, 20% methanol in dichloromethane) to give a solid (0.007 g, 13%): 1H NMR (CDCl3) δ 7.39 (m, 2H), 7.00 (s, 1H), 6.79 (dd, J=8.4, 2.4 Hz, 1H), 4.30 (dd, J=13.8, 4.8 Hz, 1H), 4.14 (dd, J=13.8, 7.8 Hz, 1H), 3.55 (m, 1H), 3.48 (bm, 4H), 1.19 (d, J=6.6 Hz, 3H); MS m/z 230 [M+H]+.

Aufarbeitung

  1. temperaturethe solution heated
  2. temperatureto reflux for 16 h
  3. temperatureto cool
  4. extractionextracted with chloroform (2×20 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by chromatography (silica, 20% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-5be2650b95374d2f996876ca16654edf
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06884816B2

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