Reaktion #156545

Reaktionsgleichung

AcOH

hydrogen

(R)-5-amino-2-(2,3-dihydroxypropyl)-6-nitroisoindoline-1,3-dione

AcOH

4-chloro-2-methoxynicotinaldehyde

→

title compound

Ausbeute 29.3%

(R)-2-(4-Chloro-2-methoxypyridin-3-yl)-6-(2,3-dihydroxypropyl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione

Ausbeute 29.3%

Lösungsmittel

MeOH

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting solution was degassed with Argon
2. 2
   Filtrationsolids were filtered off
3. 3
   Temperaturto warm up to rt
4. 4
   SonstigeSolvent was evaporated
5. 5
   Sonstigethe oily residue was purified by column chromatography (7.5% MeOH in dichloromethane)

Vorschrift

To a suspension of (R)-5-amino-2-(2,3-dihydroxypropyl)-6-nitroisoindoline-1,3-dione (0.50 g, 1.78 mmol) in 100 mL of MeOH was added 5 mL of AcOH. The resulting solution was degassed with Argon and then charged with 10% Pd/C (0.19 g, 50% wet, 0.089 mmol) and hydrogenated at 40 psi of hydrogen for 16 h. Another 5 mL of AcOH was added to the mixture and then solids were filtered off. The filtrate was cooled to −30° C. and a solution of 4-chloro-2-methoxynicotinaldehyde (0.31 g, 1.78 mmol) in 50 mL of MeOH was added dropwise under inert atmosphere. The resulting red clear solution was allowed to warm up to rt and stirred for 16 h. Solvent was evaporated and the oily residue was purified by column chromatography (7.5% MeOH in dichloromethane) to give title compound as a yellow solid (0.21 g, 29.3%). 1H NMR (500 MHz, DMSO-d6) δ 8.37 (d, J=5.5 Hz, 1H), 8.07 (s, 2H), 7.40 (d, J=5.5 Hz, 1H), 4.92 (d, J=5.0 Hz, 1H), 4.67 (br s, 1H), 4.20-4.14 (br s, 1H), 3.90 (s, 3H), 3.90-3.80 (m, 1H), 3.64-3.60 (m, 2H), 3.42-3.36 (m, 2H). ESI MS: m/z 403.1 (M+1).

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