Sodium hydride → 3-Methyl-1-benzothiophene-2-sulfonyl chloride

HRID 1693119

Reaktionsgleichung

Reaktionsgleichung von HRID 1693119
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:17]=2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[F:27][C:28]1[CH:41]=[CH:40][C:31]2[S:32][C:33]([S:36]([Cl:39])(=[O:38])=[O:37])=[C:34]([CH3:35])[C:30]=2[CH:29]=1>CS(C)=O>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][S:36]([C:33]3[S:32][C:31]4[CH:40]=[CH:41][C:28]([F:27])=[CH:29][C:30]=4[C:34]=3[CH3:35])(=[O:38])=[O:37])=[C:18]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:17]=2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:35][C:34]1[C:30]2[CH:29]=[CH:28][CH:41]=[CH:40][C:31]=2[S:32][C:33]=1[S:36]([Cl:39])(=[O:37])=[O:38]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 27745865-Fluoro-3-methylbenzo[b]thiophene-2-sulphonyl chlorideHCID 597599694-(4-Amino-3-methanesulfonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Produkt 2

HCID 27368153-Methyl-1-benzothiophene-2-sulfonyl chlorideAusbeute 321,2 %HCID 597599834-[4-(5-Fluoro-3-methyl-benzo[b]thiophene-2-sulfonylamino)-3-methanesulfonyl-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

To an ice cooled suspension of sodium hydride (60-65% in mineral oil, 0.030 g) in absolute DMSO (3 ml) was added 4-(4-amino-3-methanesulfonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (0.106 g). The mixture was stirred at 0-5° C. for 30 minutes, and a solution 5-fluoro-3-methylbenzo[b]thiophene-2-sulphonyl chloride (0.237 g) in absolute DMSO (1 ml) was added dropwise. The reaction mixture was stirred at rt for 5 h, quenched with ice/water/1 N HCl, and extracted with ethyl acetate. The organic phases were washed, dried and concentrated, and the residue was chromatographed over silica gel using heptane/ethyl acetate as eluent to obtain the desired compound (0.0.025 g) methylbenzo[b]thiophene-2-sulphonyl chloride (0.237 g) to obtain the desired compound (0.025 g) as a yellowish foam. MS (ISN): 581.3 (M−H)−

Aufarbeitung

  1. stirringThe reaction mixture was stirred at rt for 5 h
  2. customquenched with ice/water/1 N HCl
  3. extractionextracted with ethyl acetate
  4. washThe organic phases were washed
  5. customdried
  6. concentrationconcentrated
  7. customthe residue was chromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-538a651313d94fa1b407ac87d2388e92
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158655B2

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