Water → 2-phenyl-N-(7-{5-[(phenylsulfonyl)amino]-3-pyridinyl}-2-quinoxalinyl)acetamide

HRID 734964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 734964
Br[C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([NH:12][C:13](=[O:21])[CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:30]2[CH:31]=[C:32]([NH:36][S:37]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)(=[O:39])=[O:38])[CH:33]=[N:34][CH:35]=2)O1.O>C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1.[Cl-].[Na+].O>[C:15]1([CH2:14][C:13]([NH:12][C:8]2[CH:7]=[N:6][C:5]3[C:10](=[CH:11][C:2]([C:30]4[CH:35]=[N:34][CH:33]=[C:32]([NH:36][S:37]([C:40]5[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=5)(=[O:39])=[O:38])[CH:31]=4)=[CH:3][CH:4]=3)[N:9]=2)=[O:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

7

Edukt 3

HCID 962WaterHCID 52936632N-[5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]benzenesulfonamideHCID 68509491N-(7-bromo-2-quinoxalinyl)-2-phenylacetamide

Produkt 1

HCID 578433632-phenyl-N-(7-{5-[(phenylsulfonyl)amino]-3-pyridinyl}-2-quinoxalinyl)acetamideAusbeute 33,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 10340Sodium CarbonateLösungsmittelHCID 312751,4-DioxaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of N-(7-bromo-2-quinoxalinyl)-2-phenylacetamide (0.254 mmol), N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]benzenesulfonamide (0.508 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (1:1) (0.007 mmol) in 2M aqueous sodium carbonate (0.5 mL) and 1,4-dioxane (2 mL) was heated at 100° C. for 5 h. The reaction mixture was cooled, poured into water (60 mL) and brine (15 mL), and extracted with ethyl acetate (50 mL). The aqueous layer was acidified with 1N aqueous HCl until the pH was approximately 6-7 and then further extracted with (3×50 mL) ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Purification of the residue by silica gel chromatography eluting with 50-70% ethyl acetate/hexanes followed by reverse phase HPLC (30-75% acetonitrile/water with 0.1% TFA) afforded the title product as a tan solid (42 mg, 33%). MS(ES)+ m/e 496 [M+H]+.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate (50 mL)
  3. extractionfurther extracted with (3×50 mL) ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by silica gel chromatography
  8. washeluting with 50-70% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-6e6d12b4db544d718eb25537c78acfaa
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592342B2

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