Ethanol → N-(isobutoxycarbonyl)-N-(3-methoxy-5-methyl-2-pyrazinyl)-4'-methyl-2-biphenylsulphonamide

HRID 343395Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 343395
[CH2:1]([O:5][C:6]([N:8]([C:19]1[C:24]([O:25][CH3:26])=[N:23][C:22]([CH3:27])=[CH:21][N:20]=1)[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1I)(=[O:11])=[O:10])=[O:7])[CH:2]([CH3:4])[CH3:3].[C:28]1([CH3:34])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:1]([O:5][C:6]([N:8]([C:19]1[C:24]([O:25][CH3:26])=[N:23][C:22]([CH3:27])=[CH:21][N:20]=1)[S:9]([C:12]1[C:13]([C:31]2[CH:32]=[CH:33][C:28]([CH3:34])=[CH:29][CH:30]=2)=[CH:14][CH:15]=[CH:16][CH:17]=1)(=[O:11])=[O:10])=[O:7])[CH:2]([CH3:4])[CH3:3]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 1140TolueneHCID 10340Sodium CarbonateHCID 18704832N-(isobutoxycarbonyl)-N-(3-methoxy-5-methyl-2-pyrazinyl)-2-iodobenzenesulphonamide

Produkt 1

HCID 18704823N-(isobutoxycarbonyl)-N-(3-methoxy-5-methyl-2-pyrazinyl)-4'-methyl-2-biphenylsulphonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of N-(isobutoxycarbonyl)-N-(3-methoxy-5-methyl-2-pyrazinyl)-2-iodobenzenesulphonamide (0.252 g) 4-methylbenzeneboronic acid (0.068 g), tetrakis(triphenylphosphine)palladium(0) (0.0115 g), toluene (2.5 ml), ethanol (1.25 ml) and 2M sodium carbonate solution (3.75 ml) was stirred vigorously and heated under reflux for 2 hours under an atmosphere of argon. Water (10 ml) was added and the mixture was extracted with ethyl acetate (2×10 ml). The combined extracts were washed with saturated sodium chloride solution (25 ml) and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by flash chromatography, eluting with ethyl acetate/hexane (1:4 v/v), to give N-(isobutoxycarbonyl)-N-(3-methoxy-5-methyl-2-pyrazinyl)-4'-methyl-2-biphenylsulphonamide (0.182 g); 1H NMR (DMSO-d6): 0.6 (d,6H), 1.55-1.75 (m,1H), 2.35 (s,3H), 2.5 (s,3H), 3.85 (d,2H), 3.95 (s,3H), 7.15-7.25 (m,4H), 7.35-7.45 (m,1H), 7.7-7.8 (m,2H), 8.15 (s,1H), 8.45-8.55 (m,1H); mass spectrum (+ve FAB, methanol/NBA): 470 (M+H)+.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 2 hours under an atmosphere of argon
  3. extractionthe mixture was extracted with ethyl acetate (2×10 ml)
  4. washThe combined extracts were washed with saturated sodium chloride solution (25 ml)
  5. dry with materialdried (MgSO4)
  6. customVolatile material was removed by evaporation
  7. customthe residue was purified by flash chromatography
  8. washeluting with ethyl acetate/hexane (1:4 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-a5c6cecccdf3447298e457977ff59b9b
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05861401

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