Реакция #45471

Уравнение реакции

3-(4-amino-3-methoxyphenyl)-7-iodofuro[3,2-c]pyridin-4-amine

1-methyl-1H-2-indolecarbonyl chloride

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title compound

Выход 89.7%

N-[4-(4-amino-7-iodofuro[3,2-c]pyridin-3-yl)-2-methoxyphenyl]-1-methyl-1H-indole-2-carboxamide

Выход 89.7%

Растворители

pyridine

Условия реакции

Обработка

1. 1
   workup.WAITto rise to ambient temperature over an 18 hour
2. 2
   ДругоеThe solvent was removed in vacuo
3. 3
   workup.DISSOLUTIONthe residue was dissolved in water (50 mL)
4. 4
   Другоеformed
5. 5
   ЭкстракцияThe suspension was extracted with dichloromethane (4×25 mL)
6. 6
   Промывкаthe combined organic layers were washed with brine (25 mL)
7. 7
   Сушкаdried over anhydrous magnesium sulfate
8. 8
   ДругоеThe solvent was removed in vacuo

Методика

A solution of 3-(4-amino-3-methoxyphenyl)-7-iodofuro[3,2-c]pyridin-4-amine (2.53 g, 6.65 mmol) in pyridine (30 mL) was cooled to 0° C. and 1-methyl-1H-2-indolecarbonyl chloride (2.57 g, 13.3 mmol) was added. The mixture was stirred for 15 minutes at 0° C. and then allowed to rise to ambient temperature over an 18 hour time period. The solvent was removed in vacuo and the residue was dissolved in water (50 mL) and brought to pH 12 with 0.1 N aqueous sodium hydroxide, at which point a precipitate formed. The suspension was extracted with dichloromethane (4×25 mL) and the combined organic layers were washed with brine (25 mL) and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to give the title compound (3.21 g, 89%) as a yellow solid. 1H NMR (DMSO-d6, 400 MHz) δ 9.48 (s, 1H), 8.14 (s, 1H), 8.08 (s, 1H), 8.04 (t, 1H), 7.71 (d, 1H), 7.59 (d, 1H), 7.30-7.37 (m, 2H), 7.25 (d, 1H), 7.11-7.18 (m, 2H), 5.75-5.83 (bs, 2H), 4.04 (s, 3H), 3.93 (s, 3H); RP-HPLC (Conditions d) Rt 8.73 min.; MS: MH+ 539.

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