Реакция #156545

Уравнение реакции

AcOH

hydrogen

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

AcOH

4-chloro-2-methoxynicotinaldehyde

→

title compound

Выход 29.3%

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

Выход 29.3%

Растворители

MeOH

MeOH

Условия реакции

Обработка

1. 1
   ДругоеThe resulting solution was degassed with Argon
2. 2
   Фильтрацияsolids were filtered off
3. 3
   Температураto warm up to rt
4. 4
   ДругоеSolvent was evaporated
5. 5
   Другоеthe oily residue was purified by column chromatography (7.5% MeOH in dichloromethane)

Методика

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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