Triethylamine → 2-Bromo-3-(3,5-difluorophenyl)-6-{2-[1-(methylsulfonyl)piperidin-4-yl]ethoxy}-1H-inden-1-one

HRID 331348Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 331348
C([C:5]1[CH:13]=[C:12]([O:14][CH2:15][CH2:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH:11]=[C:10]2[C:6]=1[C:7]([C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([F:32])[CH:26]=1)=[C:8]([Br:24])[C:9]2=[O:23])(C)(C)C.C(N(CC)CC)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl>[Br:24][C:8]1[C:9](=[O:23])[C:10]2[C:6]([C:7]=1[C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([F:32])[CH:26]=1)=[CH:5][CH:13]=[C:12]([O:14][CH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([S:41]([CH3:40])(=[O:43])=[O:42])[CH2:19][CH2:18]1)[CH:11]=2

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 70315845t-butyl 6-(2-(piperidin-4-yl)ethoxy)-2-bromo-3-(3,5-difluorophenyl)-1H-inden-1-one

Produkt 1

HCID 703089562-Bromo-3-(3,5-difluorophenyl)-6-{2-[1-(methylsulfonyl)piperidin-4-yl]ethoxy}-1H-inden-1-oneAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of t-butyl 6-(2-(piperidin-4-yl)ethoxy)-2-bromo-3-(3,5-difluorophenyl)-1H-inden-1-one (211 mg, 1.2 eq, 1.03 mmol) obtaind in Step 2 in CH2Cl2 at 0° C. was added triethylamine (1.5 eq) and methylsulfonyl chloride (1.0 eq). The mixture was stirred for 1 h at room temperature and diluted with CH2Cl2. The mixture was washed with H2O and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexanes=1:1) to obtain the title compound (58%).

Aufarbeitung

  1. washThe mixture was washed with H2O and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (EtOAc/hexanes=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-fc7c7d27a2224cdf86f21a8ad532deac
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877747B2

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