반응 #88613

반응 방정식

benzyl chloroformate

Sodium hydride

3-bromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrol-5-ol

→

title compound

수율 17.0%

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

수율 17.0%

용매

DMF

DMF

반응 조건

후처리

1. 1
   온도a cooled
2. 2
   workup.ADDITIONOn complete addition the mixture
3. 3
   workup.STIRRINGstirred for 15 minutes
4. 4
   workup.STIRRINGstirring
5. 5
   workup.WAITcontinued for 18 hours
6. 6
   기타The solvent was evaporated
7. 7
   workup.ADDITIONthe resultant residue diluted with water
8. 8
   추출extracted with dichloromethane (5×50 mL) and ethyl acetate (3×30 mL)
9. 9
   건조The combined organic layer was dried over (Na2SO4)
10. 10
    여과filtered
11. 11
    기타evaporated
12. 12
    기타to afford a residue
13. 13
    기타The resultant residue was purified by flash chromatography (silica, 12 g cartridge, ISCO, 0-7% methanol in dichloromethane)
14. 14
    기타The appropriate fractions were collected
15. 15
    기타evaporated

실험 절차

Sodium hydride (167 mg, 4.17 mmol) was added to a cooled (0° C.) mixture of 3-bromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrol-5-ol (1.0 g, 3.79 mmol) in DMF (15 mL). On complete addition the mixture was stirred for 15 minutes then allowed to warm to ambient temperature and stirred for 15 minutes. A solution of benzyl chloroformate (610 mg, 3.6 mmol) in DMF (1 mL) was added and stirring continued for 18 hours. The solvent was evaporated and the resultant residue diluted with water and extracted with dichloromethane (5×50 mL) and ethyl acetate (3×30 mL). The combined organic layer was dried over (Na2SO4), filtered and evaporated to afford a residue. 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 a light yellow solid (240 mg, 17%). LCMS (Method B): RT=4.54 min, M+H+=398/400. 1H NMR (400 MHz, DMSO-d6): 8.99 (s, 1H), 8.79 (d, J=2.4 Hz, 1H), 8.63 (d, J=2.4 Hz, 1H), 8.23 (s, 1H), 7.63 (d, J=7.5 Hz, 2H), 7.48-7.36 (m, 3H), 5.61 (s, 2H).

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