Sodium Carbonate → N-(5-chloro-1,3-thiazol-2-yl)-3-cyano-4-[4-fluoro-2-(1H-pyrazol-4-yl)phenoxy]benzenesulfonamide

HRID 1692199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1692199
[Cl:1][C:2]1[S:6][C:5]([NH:7][S:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3I)=[C:13]([C:26]#[N:27])[CH:12]=2)(=[O:10])=[O:9])=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:36]2[CH:37]=[N:38][NH:39][CH:40]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O>[Cl:1][C:2]1[S:6][C:5]([NH:7][S:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[C:36]3[CH:37]=[N:38][NH:39][CH:40]=3)=[C:13]([C:26]#[N:27])[CH:12]=2)(=[O:10])=[O:9])=[N:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 59436633N-(5-chloro-1,3-thiazol-2-yl)-3-cyano-4-(4-fluoro-2-iodophenoxy)benzenesulfonamide

Produkt 1

HCID 46840816N-(5-chloro-1,3-thiazol-2-yl)-3-cyano-4-[4-fluoro-2-(1H-pyrazol-4-yl)phenoxy]benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21962138N,N-Dimethylformamide--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

N-(5-Chloro-1,3-thiazol-2-yl)-3-cyano-4-(4-fluoro-2-iodophenoxy)benzenesulfonamide (Preparation 240, 50 mg, 0.09 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (27 mg, 0.14 mmol) palladium (0) tetrakis(triphenylphosphine) (10 mg, 0.009 mmol) and sodium carbonate (30 mg, 0.28 mmol) were dissolved in dimethylformamide:water (2:1, 1.5 ml.) and heated to 90° C. for 18 hours. The reaction was partitioned between ethyl acetate and saturated aqueous sodium chloride solution. The organic layer was separated, dried over sodium sulfate and evaporated in vacuo to afford a brown oil. Purification by preparative HPLC afforded the title compound. Yield 12.5 mg 30%.

Aufarbeitung

  1. customThe reaction was partitioned between ethyl acetate and saturated aqueous sodium chloride solution
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customto afford a brown oil
  6. customPurification by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-1e730463135e4e7cbe24f4b4bba29dce
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153814B2

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