Ammonium Chloride → (1-(4-Fluorobenzyl)-5-methanesulfonylindol-2-yl)(thiazol-2-yl)-methanol

HRID 1838372

Reaktionsgleichung

Reaktionsgleichung von HRID 1838372
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C([Li])CCC.[F:12][C:13]1[CH:34]=[CH:33][C:16]([CH2:17][N:18]2[C:26]3[C:21](=[CH:22][C:23]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:24][CH:25]=3)[CH:20]=[C:19]2[CH:31]=[O:32])=[CH:15][CH:14]=1.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[F:12][C:13]1[CH:34]=[CH:33][C:16]([CH2:17][N:18]2[C:26]3[C:21](=[CH:22][C:23]([S:27]([CH3:30])(=[O:28])=[O:29])=[CH:24][CH:25]=3)[CH:20]=[C:19]2[CH:31]([C:2]2[S:3][CH:4]=[CH:5][N:6]=2)[OH:32])=[CH:15][CH:14]=1

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 764302-BromothiazoleHCID 225043741-(4-Fluorobenzyl)-5-methanesulfonylindole-2-carbaldehydeHCID 178418339Butyllithium

Produkt 1

HCID 22504451(1-(4-Fluorobenzyl)-5-methanesulfonylindol-2-yl)(thiazol-2-yl)-methanolAusbeute 28,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a mixture of 2-bromothiazole (123 mg) and tetrahydrofuran (3.5 ml), 1.61 M n-butyl lithium solution in hexane (0.51 ml) was added at −78° C. and the mixture was stirred for 30 minutes, followed by addition of a solution of 1-(4-fluorobenzyl)-5-methanesulfonylindole-2-carbaldehyde (50 mg) obtained in Example 27 (4) in tetrahydrofuran (3.5 ml) at the same temperature, and the mixture was stirred as such for 30 minutes. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, extracted with chloroform, washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel preparative thin-layer chromatography (hexane:ethyl acetate=1:1) to obtain 18 mg of the desired product as a yellow oil.

Aufarbeitung

  1. additionwas added at −78° C.
  2. stirringthe mixture was stirred as such for 30 minutes
  3. extractionextracted with chloroform
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b0fa781fa3c848a0b46f404771dc8c8b
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06673797B1

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