Water → HCID 178471465, Verbindung

HRID 468638

Reaktionsgleichung

Reaktionsgleichung von HRID 468638
[F:1][C:2]1[C:3](I)=[CH:4][C:5](=[O:21])[N:6]([CH2:8][CH2:9][C@@:10]([CH3:20])([S:16]([CH3:19])(=[O:18])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=1.CC1(C)C(C)(C)OB([C:31]2[CH:51]=[CH:50][C:34]([O:35][CH2:36][C@H:37]3[CH2:42][CH2:41][C@H:40]([O:43][CH:44]4[CH2:49][CH2:48][CH2:47][CH2:46][O:45]4)[CH2:39][CH2:38]3)=[CH:33][CH:32]=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>CC1CCCO1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:1][C:2]1[C:3]([C:31]2[CH:51]=[CH:50][C:34]([O:35][CH2:36][C@H:37]3[CH2:38][CH2:39][C@H:40]([O:43][CH:44]4[CH2:49][CH2:48][CH2:47][CH2:46][O:45]4)[CH2:41][CH2:42]3)=[CH:33][CH:32]=2)=[CH:4][C:5](=[O:21])[N:6]([CH2:8][CH2:9][C@@:10]([CH3:20])([S:16]([CH3:19])(=[O:18])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 67249679Ethyl (2R)-4-(5-fluoro-4-iodo-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoateHCID 178431083HCID 178431083, Verbindung

Produkt 1

HCID 178471465HCID 178471465, VerbindungAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 67831299Water methyl tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Pd(dppf)Cl2 (350 mg, 0.431 mmol) was added to a solution of ethyl (2R)-4-(5-fluoro-4-iodo-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoate (1.6 g, 3.6 mmol), 2-[(trans-4-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]methyl}cyclohexyl)oxy]tetrahydro-2H-pyran (1.9 g, 4.49 mmol), and potassium phosphate tribasic (2.9 g, 10.8 mmol) in 2-methyl tetrahydrofuran/water (5:1, 240 mL). The reaction mixture was heated to 80° C. and stirred at this temperature for 16 h. The reaction was allowed to cool to rt, and water (50 mL) was added. The mixture was extracted with EtOAc (3×150 mL). The combined organic phases were dried (Na2SO4), filtered, and concentrated under reduced pressure to afford the title compound as a light tan solid (1.4 g, 64%). MS (LCMS) m/z 608.2 (M+1).

Aufarbeitung

  1. temperatureto cool to rt
  2. extractionThe mixture was extracted with EtOAc (3×150 mL)
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f909ed890a6b412d84a1c3fea6e84497
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08624034B2

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