Sodium Dithionite → 6-Bromo-2-(4-methoxyphenyl)-7-(4-(pyridin-3-ylmethyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridine

HRID 416738

Reaktionsgleichung

Reaktionsgleichung von HRID 416738
[Br:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[CH2:14][CH2:13]2)=[C:4]([N+:9]([O-])=O)[C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(O)C>[Br:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[CH2:14][CH2:13]2)=[C:4]2[N:9]=[C:31]([C:30]3[CH:33]=[CH:34][C:27]([O:26][CH3:25])=[CH:28][CH:29]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 24489Sodium DithioniteHCID 312444-MethoxybenzaldehydeHCID 468687795-Bromo-3-nitro-4-(4-(pyridin-3-ylmethyl)piperazin-1-yl)pyridin-2-amine

Produkt 1

HCID 1784888706-Bromo-2-(4-methoxyphenyl)-7-(4-(pyridin-3-ylmethyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a mixture of 5-bromo-3-nitro-4-(4-(pyridin-3-ylmethyl)piperazin-1-yl)pyridin-2-amine (0.043 g, 0.11 mmol) and ethanol (2.4 ml) was added 4-methoxybenzaldehyde (0.024 g, 0.18 mmol) with the aid of ethanol (1 ml) followed by a freshly prepared aqueous solution of Na2S2O4 (1M; 0.44 ml, 0.44 mmol). The reaction mixture was heated at 70° C. for 4.5 h, then allowed to cool to room temperature and the solvents were removed in vacuo. The residue was absorbed on silica gel and the free running powder was placed on a 10 g isolute silica column which was eluted with 50% ethyl acetate in dichloromethane, and then 3% to 6% methanol in ethyl acetate/dichloromethane (v/v; 1:1). The title compound was obtained as a yellow solid after trituration with diethyl ether (0.015 g, 28%); 1H-NMR (500 MHz, DMSO-d6) 2.62 (br s, 4H, piperazine N(CH2)2), 3.62 (s, 2H, NCH2CO), 3.66 (br s, 4H, piperazine N(CH2)2), 3.84 (s, 3H, OCH3), 7.10 (d, J=8.89 Hz, 2H) and 8.14 (d, J=8.57 Hz, 2H) (3,5-C6H4OMe and 2,6-C6H4—OMe), 7.39 (dd, J=7.91, 5.08 Hz, 1H, pyridyl 5-H), 7.76 (d, J=7.80 Hz, 1H, pyridyl 4-H), 8.20 (s, 1H, imidazo[4,5-b]pyridine 5-H), 8.50 (dd, J=4.76, 1.58 Hz, 1H, pyridyl 6-H), 8.56 (d, J=1.62 Hz, 1H, pyridyl 2-H), 13.37 (s, 1H, imidazo[4,5-b]pyridine N—H);

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customthe solvents were removed in vacuo
  3. customThe residue was absorbed on silica gel
  4. washwas eluted with 50% ethyl acetate in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-04cb507fec53434c8df14feccd563fcd
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088761B2

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