Toluene → 4-(4-isobutylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)-N-[2-(trimethylsilyl)ethoxymethyl]pyridine-3-sulphonamide

HRID 361426

Reaktionsgleichung

Reaktionsgleichung von HRID 361426
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[S:8]([N:11]([C:20]1[C:25]([O:26][CH3:27])=[N:24][C:23]([CH3:28])=[CH:22][N:21]=1)[CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])(=[O:10])=[O:9].[CH2:29]([C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1)[CH:30]([CH3:32])[CH3:31].C1(C)C=CC=CC=1.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.CCOCC.C(O)C>[CH2:29]([C:33]1[CH:38]=[CH:37][C:36]([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[S:8]([N:11]([C:20]2[C:25]([O:26][CH3:27])=[N:24][C:23]([CH3:28])=[CH:22][N:21]=2)[CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])(=[O:10])=[O:9])=[CH:35][CH:34]=1)[CH:30]([CH3:32])[CH3:31]

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2773472(4-Isobutylphenyl)boronic acidHCID 21186278HCID 21186278, Verbindung

Produkt 1

HCID 211862384-(4-isobutylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)-N-[2-(trimethylsilyl)ethoxymethyl]pyridine-3-sulphonamideAusbeute 77,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Tetrakis(triphenylphosphine)palladium(0) (0.018 g) was added to a deoxygenated mixture of 4-chloro-N-(3-methoxy-5-methylpyrazin-2-yl)-N-[2(trimethylsilyl) ethoxymethyl]pyridine-3-sulphonamide (0.225 g), 4-isobutylphenylboronic acid (0.109 g), toluene (4 ml), ethanol (2 ml) and 2M sodium carbonate solution (6 ml) and the mixture was stirred and heated under reflux for 18 hours. Ether (25 ml) was added and the mixture was washed with water (2×25 ml) and saturated sodium chloride solution. Aqueous layers were back-extracted with ether (25 ml). The organic extracts were combined and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by gradient elution with 25-50% ethyl acetate/hexane through a silica gel Mega Bond Elut column to give 4-(4-isobutylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)-N-[2-(trimethylsilyl)ethoxymethyl]-pyridine-3-sulphonamide (0.213 g) as an oil; 1H NMR (d6 -DMSO): -0.1 (s, 9 H), 0.7 (t, 2 H), 0.9 (d, 6 H), 1.9 (m, 1 H), 2.45 (s, 3 H), 2.5 (d, 2 H), 3.5 (t, 2 H), 3.8 (s, 3 H), 4.7 (s, 2 H), 7.2 (d, 2 H), 7.3 (d, 2 H), 7.4 (d, 1 H), 8.0 (s, 1 H), 8.8 (d, 1 H), 9.2 (s, 1 H); mass spectrum (+ve ESP): 543 (M+H)+.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 18 hours
  3. washthe mixture was washed with water (2×25 ml) and saturated sodium chloride solution
  4. extractionAqueous layers were back-extracted with ether (25 ml)
  5. dry with materialdried (MgSO4)
  6. customVolatile material was removed by evaporation
  7. customthe residue was purified by gradient elution with 25-50% ethyl acetate/hexane through a silica gel Mega Bond Elut column

Quellen und Nachweise

ORD-Eintrag
ord-a975d4131b974a2bac5be506f3fa8f3f
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866568

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