Benzyl Bromide → HCID 9967388, Verbindung

HRID 1711601Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1711601
[CH3:1][O:2][C:3]([C:5]1[O:9][C:8]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][N:11]=2)=[CH:7][CH:6]=1)=[O:4].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[H-].[Na+]>C1COCC1>[CH2:19]([N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([C:8]2[O:9][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=2)=[N:11]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 9856210HCID 9856210, Verbindung

Produkt 1

HCID 9967388HCID 9967388, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 3-(5-methoxycarbonyl-2-furyl)-1H-indazole (2.0 g, 8.3 mmol) and benzyl bromide (2.5 mL, 21.0 mmol) in THF (100 mL) was added dropwise via dropping funnel to a suspension of sodium hydride (60% dispersion in oil: 0.50 g, 12.5 mmol) in THF (200 mL). The resultant mixture was stirred at room temperature for 20 h. The mixture was poured onto brine and the layers separated. The aqueous layer was extracted three times with ether and then the combined organic material was washed with saturated aqueous NaHCO3 solution, dried (MgSO4) and concentrated under reduced pressure. The residue was chromatographed on silica (EtOAc:cyclohexane 1:4) and then the product was recrystallised (EtOAc/hexane) to give a yellow solid: mp 137-138° C.; MS (EI) M30 332; 1H-NMR (CDCl3) 3.97 (s, 3H), 5.67 (s, 2H), 7.03 (d, 1H, J=3.7 Hz), 7.22-7.43 (m, 9H), 8.27 (d, 1H, J=8.1 Hz); Anal. (C20H16N2O3) C, calcd 72.28; found 71.92, H, calcd 4.85; found 4.75, N, calcd 8.43; found 8.39.

Aufarbeitung

  1. additionThe mixture was poured onto brine
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted three times with ether
  4. washthe combined organic material was washed with saturated aqueous NaHCO3 solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on silica (EtOAc:cyclohexane 1:4)
  8. customthe product was recrystallised (EtOAc/hexane)
  9. customto give a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-173c74679d4f4e7da09eca76958b88db
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790761B2

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