Acetic Acid → HCID 178480352, Verbindung

HRID 428564

Reaktionsgleichung

Reaktionsgleichung von HRID 428564
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[F:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([CH3:28])[CH:23]=[C:22]2[CH:29]1[CH2:34][CH2:33][C:32](=O)[CH2:31][CH2:30]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClC(Cl)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N:12]3[CH2:17][CH2:16][N:15]([C@H:32]4[CH2:31][CH2:30][C@@H:29]([C:22]5[C:21]6[C:25](=[CH:26][CH:27]=[C:19]([F:18])[CH:20]=6)[N:24]([CH3:28])[CH:23]=5)[CH2:34][CH2:33]4)[CH2:14][CH2:13]3)[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 184140594-(5-fluoro-1-methyl-1H-indol-3-yl)-cyclohexanoneHCID 184140636-Bromo-8-piperazin-1-yl-quinoline

Produkt 1

HCID 178480352HCID 178480352, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-80d4d186d76f4258b0f6708d2ff5d583
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313126B1

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