8-Bromo-2-(5-tert-butyl-[1,2,3]triazol-1-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene → 2-(5-tert-Butyl-[1,2,3]triazol-1-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

HRID 2079035Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2079035
Br[C:2]1[CH:24]=[CH:23][C:5]2[C:6]3[N:7]=[C:8]([N:14]4[C:18]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:17][N:16]=[N:15]4)[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1>CO.[Pd]>[C:19]([C:18]1[N:14]([C:8]2[S:9][C:10]3[CH2:11][CH2:12][O:13][C:4]4[CH:3]=[CH:2][CH:24]=[CH:23][C:5]=4[C:6]=3[N:7]=2)[N:15]=[N:16][CH:17]=1)([CH3:22])([CH3:20])[CH3:21]

Komponenten

4

Edukt 1

HCID 579003598-Bromo-2-(5-tert-butyl-[1,2,3]triazol-1-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

Produkt 1

HCID 532349762-(5-tert-Butyl-[1,2,3]triazol-1-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azuleneAusbeute 66,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A suspension of 8-bromo-2-(5-tert-butyl-[1,2,3]triazol-1-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene (101 mg, 0.25 mmol) and 10% Pd/C (250 mg) in MeOH (5 mL) was stirred at RT under a hydrogen atmosphere for 16 h. The reaction mixture was flushed with nitrogen, filtered through Celite, washed with ethyl acetate and concentrated in vacuo. The resulting residue was purified by flash chromatography (SiO2, 20% ethyl acetate in cyclohexane) to give 434 as a white solid (54 mg, 66%). LCMS (Method C): RT=13.19 min, [M+H]+=327. 1H NMR (CDCl3): 8.30 (1H, dd, J=7.9, 1.8 Hz), 7.55 (1H, s), 7.29 (1H, m), 7.17-7.12 (1H, m), 7.08 (1H, dd, J=8.0, 1.4 Hz), 4.43 (2H, t, J=5.1 Hz), 3.39 (2H, t, J=5.1 Hz), 1.55 (9H, s).

Aufarbeitung

  1. customThe reaction mixture was flushed with nitrogen
  2. filtrationfiltered through Celite
  3. washwashed with ethyl acetate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by flash chromatography (SiO2, 20% ethyl acetate in cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-c2a53da5d6ad4d31b0e1a84e0a062afa
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928248B2

Notizen zur Reaktion

Wird geladen…