反应详情

To a solution of 6-methoxy-8-piperazin-1-yl-[1,7]naphthyridine (250 mg, 1.02 mmol), 4-(5-cyano-1-methyl-1H-indol-3-yl)-cyclohexanone (260 mg, 1.02 mmol), and sodium triacetoxyborohydride (320 mg, 1.53 mmol) in dichloroethane (50 mL) was added acetic acid (0.12 mL, 2.04 mmol) and stirred overnight at room temperature. The reaction was quenched with 1 M NaOH (50 mL) then extracted in CH2Cl2 (1×50 mL) and EtOAc (75 mL). The organic fractions were combined, dried over Na2SO4, concentrated, filtered and chromatographed (5% MeOH/EtOAc+NH4OH) affording 160 mg (33%) of the cis isomer as a yellow foam. The HCl salt was generated form EtOAc affording a pale yellow solid: mp 235-238° C.

1. customThe reaction was quenched with 1 M NaOH (50 mL)
2. extractionthen extracted in CH2Cl2 (1×50 mL)
3. dry with materialdried over Na2SO4
4. concentrationconcentrated
5. filtrationfiltered
6. customchromatographed (5% MeOH/EtOAc+NH4OH)
7. customaffording 160 mg (33%) of the cis isomer as a yellow foam