1,2-Dimethoxyethane → N,N-diallyl-4-(3-(5-chloro-6-methoxypyridin-3-yl)phenylsulfonamido)pyridine-3-sulfonamide

HRID 2283343Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2283343
[CH2:1]([N:4]([CH2:25][CH:26]=[CH2:27])[S:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[NH:14][S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20](Br)[CH:19]=1)(=[O:17])=[O:16])(=[O:7])=[O:6])[CH:2]=[CH2:3].[Cl:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[N:33][C:34]=1[O:35][CH3:36].C(=O)([O-])[O-].[Cs+].[Cs+].COCCOC>Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[CH2:1]([N:4]([CH2:25][CH:26]=[CH2:27])[S:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[NH:14][S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:31]2[CH:32]=[N:33][C:34]([O:35][CH3:36])=[C:29]([Cl:28])[CH:30]=2)[CH:19]=1)(=[O:17])=[O:16])(=[O:7])=[O:6])[CH:2]=[CH2:3]

Komponenten

7

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 24901777(5-Chloro-6-methoxypyridin-3-yl)boronic acidHCID 57750923N,N-diallyl-4-(3-bromophenylsulfonamido)pyridine-3-sulfonamide

Produkt 1

HCID 57750978N,N-diallyl-4-(3-(5-chloro-6-methoxypyridin-3-yl)phenylsulfonamido)pyridine-3-sulfonamideAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of N,N-diallyl-4-(3-bromophenylsulfonamido)pyridine-3-sulfonamide (0.29 g, 0.62 mmol), 5-chloro-6-methoxypyridin-3-ylboronic acid (0.15 g, 0.81 mmol), (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.026 g, 0.030 mmol), cesium carbonate (0.30 g, 0.93 mmol), 1,2-dimethoxyethane (4.5 mL) and water (0.5 mL) under an atmosphere of argon was heated at 100° C. for 15 min in a microwave reactor. The reaction mixture was partitioned between ethyl acetate and diluted hydrochloric acid, the organic phase was dried over magnesium sulfate and the solvent was evaporated. Purification by column chromatography, using chloroform/methanol (98:2) as the eluent, gave the title compound in 58% yield.

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and diluted hydrochloric acid
  2. dry with materialthe organic phase was dried over magnesium sulfate
  3. customthe solvent was evaporated
  4. customPurification by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fdc6b04dd0de4f7baf7ddd51aadebe30
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09145380B2

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