Water → 6-(Azidomethyl)-1-(2-tetrahydropyranyl)indazole
Reaktionsgleichung
Br[CH2:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[N:8][N:9]2[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)=[CH:5][CH:4]=1.[N-:18]=[N+:19]=[N-:20].[Na+].O>CN(C=O)C>[N:18]([CH2:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[N:8][N:9]2[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)=[CH:5][CH:4]=1)=[N+:19]=[N-:20]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
To a solution of 6-(bromomethyl)-1-(2-tetrahydropyranyl)indazole (4.0 g, 14 mmol) (6) in DMF (30 mL) was added sodium azide (6 g, 92 mmol) in one portion. The suspension was heated at 90° C. for 30 minutes and a yellow solution was formed. After cooling to room temperature, the reaction mixture was poured into water (100 mL) and extracted with ether (2×150 mL). Combined organic layers were washed with brine then dried (MgSO4). Evaporation of solvent gave an yellow oil which was purified by column chromatography to yield title compound (2.91 g, 83%). TLC Rf 0.31 (70:30 of hexane-ethyl acetate); MS (electrospray) 258 (M+1); 1H NMR (CDCl3) δ1.75 (m, 3H), 2.10 (m, 2H), 2.55 (m, 1H), 3.72 (m, 1H), 4.01 (m, 1H), 4.48 (s, 2H), 5.73 (dd, 1H, J=8.2, 2.8 Hz), 7.12 (dd, 1H, J=8.2, 0.8 Hz), 7.55 (s, 1H), 7.71 (d, 1H, J=8.2 Hz), 8.02 (s, 1H).
Aufarbeitung
- customa yellow solution was formed
- temperatureAfter cooling to room temperature
- extractionextracted with ether (2×150 mL)
- washCombined organic layers were washed with brine
- dry with materialthen dried (MgSO4)
- customEvaporation of solvent
- customgave an yellow oil which
- customwas purified by column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-3dbd32136c134501a5aa1f4041b088e8
- Quelldatensatz
- uspto-grants-2003_01
- Patentnummer
- US06506754B1
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