Reaktion #2299129

Reaktionsgleichung

aldehyde

2-(1H-Indazol-3-yl)-1H-indole-5-carbaldehyde

N-methylpiperazine

acetic acid

sodium triacetoxyborohydride

→

desired product ( 6-4 )

3-[5-(4-Methyl-piperazin-1-ylmethyl)-1H-indol-2-yl]-1H-indazole

Lösungsmittel

N,N-dimethyl formamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was partitioned between ethyl acetate and water
2. 2
   WaschenThe organic layer was washed with brine
3. 3
   Sonstigeseparated
4. 4
   Trocknendried (MgSO4)
5. 5
   Einengenconcentrated in vacuo

Vorschrift

A mixture of the aldehyde (6-3, 50 mg, 0.19 mmol), N-methylpiperazine (191 mg, 1.91 mmol), acetic acid (0.06 mL) and sodium triacetoxyborohydride (406 mg, 1.91 mmol) in N,N-dimethyl formamide (3 mL) was stirred at the ambient temperature for 11 h. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, separated, dried (MgSO4) and concentrated in vacuo. Chromatography (SiO2, 30% methanol in ethyl acetate) afforded the desired product (6-4) as a light tan solid; 1H NMR (400 MHz, DMSO-d6) δ 13.34 (s, 1H), 11.56 (s, 1H), 8.23 (d, 1H, J=8.0 Hz), 7.66 (d, 1H, J=8.4 Hz), 7.53 (s, 1H), 7.49 (t, 1H, J=7.6 Hz), 7.44 (d, 1H, J=8.4 Hz), 7.31 (t, 1H, J=7.6 Hz), 7.12–7.11 (m, 2H), 3.57 (s, 2H), 2.52–2.26 (m, 8H), 2.21 (s, 3H).

Quelle