تفاعل #88614

معادلة التفاعل

3-bromo-5-hydroxy-dipyrido[2,3-b;4′,3′-d]pyrrole-9-carboxylic acid benzyl ester

4-hydroxypiperidine-1-carboxylic acid tert-butyl ester

triphenylphosphine

diethyl azodicarboxylate

→

title compound

المردود 100.0%

3-Bromo-5-(1-tert-butoxycarbonyl-piperidin-4-yloxy)-dipyrido[2,3-b;4′,3′-d]pyrrole-9-carboxylic acid benzyl ester

المردود 100.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONOn complete addition the mixture
2. 2
   تركيزThe mixture was concentrated in-vacuo
3. 3
   أخرىthe resultant residue was purified by flash chromatography (silica, 12 g cartridge, ISCO, 0-7% methanol in dichloromethane)
4. 4
   أخرىThe appropriate fractions were collected
5. 5
   أخرىevaporated

الإجراء التجريبي

A solution of 3-bromo-5-hydroxy-dipyrido[2,3-b;4′,3′-d]pyrrole-9-carboxylic acid benzyl ester (234 mg, 0.59 mmol), 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (295 mg, 1.47 mmol) and triphenylphosphine (390 mg, 1.47 mmol) in anhydrous THF (7 mL) was treated dropwise with diethyl azodicarboxylate (295 mg, 1.47 mmol). On complete addition the mixture was heated at 50° C. for 1 hour. The mixture was concentrated in-vacuo and the resultant residue was purified by flash chromatography (silica, 12 g cartridge, ISCO, 0-7% methanol in dichloromethane). The appropriate fractions were collected and evaporated to afford the title compound as an orange oil (0.34 g, 100%). LCMS (Method B): RT=4.76 min, M+H+=581/583. 1H NMR (400 MHz, CDCl3): 9.27 (s, 1H), 8.80 (d, J=2.3 Hz, 1H), 8.61 (d, J=2.3 Hz, 1H), 8.32 (s, 1H), 7.60 (d, J=7.3 Hz, 2H), 7.43-7.36 (m, 3H), 5.64 (s, 2H), 4.89 (m, 1H), 3.40-3.39 (m, 2H), 3.02 (ddd, J=13.5, 9.8, 3.4 Hz, 2H), 2.21-1.80 (m, 4H), 1.46 (s, 9H).

المصدر