Acetic Acid → HCID 178480352, compound

To a solution of 6-bromo-8-piperazin-1-yl-quinoline (610 mg, 2.09 mmol), 4-(5-fluoro-1-methyl-1H-indol-3-yl)-cyclohexanone (510 mg, 2.09 mmol), and sodium triacetoxyborohydride (660 mg, 3.14 mmol) in dichloroethane (40 mL) was added acetic acid (0.24 mL, 4.18 mmol) and stirred overnight at room temperature. The reaction was quenched with 1 M NaOH (50 mL) and H2O (100 mL) then extracted in CH2Cl2 (100 mL) and EtOAc (100 mL). The organic fractions were combined, dried over Na2SO4, concentrated, filtered and chromatographed (5% MeOH/EtOAc). The majority of the cis compound precipitated out of 5% MeOH/EtOAc before application to the column and was purified by filtration affording 510 mg (47%) of the cis isomer as a pale yellow solid: mp 215-217° C.

1. customThe reaction was quenched with 1 M NaOH (50 mL) and H2O (100 mL)
2. extractionthen extracted in CH2Cl2 (100 mL)
3. dry with materialdried over Na2SO4
4. concentrationconcentrated
5. filtrationfiltered
6. customchromatographed (5% MeOH/EtOAc)
7. customThe majority of the cis compound precipitated out of 5% MeOH/EtOAc before application to the column
8. filtrationwas purified by filtration
9. customaffording 510 mg (47%) of the cis isomer as a pale yellow solid

ORD record

ord-c338ce27f5884a1197995610edd2d849

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06465482B2