Reacción #649229

Ecuación de reacción

NaBH(OAc)3

3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide

4-(aminomethyl)-1,2-benzenediol

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title compound

Rendimiento 15.1%

5-[3-({[(3,4-dihydroxyphenyl)methyl]amino}methyl)phenyl]-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide

Rendimiento 15.1%

Disolventes

dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe resulting mixture was shaken overnight at ambient temperature after which time the solvent
2. 2
   Otrowas removed under reduced pressure
3. 3
   OtroThe crude product was purified by reverse phase HPLC (water/CH3CN, 0.1% TFA 10-90%)

Procedimiento

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide (50 mg, 0.114 mmol) in dichloroethane (2 mL) was added 4-(aminomethyl)-1,2-benzenediol (12.1 mg, 0.087 mmol). The reaction solution was stirred at ambient temperature for 10 min prior to addition of NaBH(OAc)3 (58 mg, 0.261 mmol). The resulting mixture was shaken overnight at ambient temperature after which time the solvent was removed under reduced pressure. The crude product was purified by reverse phase HPLC (water/CH3CN, 0.1% TFA 10-90%) to give the title compound (7.4 mg, 12%).

Fuente