Reacción #45471

Ecuación de reacción

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

1-methyl-1H-2-indolecarbonyl chloride

→

title compound

Rendimiento 89.7%

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

Rendimiento 89.7%

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente