Water → HCID 67248183, Verbindung

HRID 84294

Reaktionsgleichung

Reaktionsgleichung von HRID 84294
C(=O)([O-])[O-].[K+].[K+].[C:7]1(B(O)O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[F:16][C:17]1[C:18](I)=[CH:19][C:20](=[O:36])[N:21]([CH2:23][CH2:24][C@@:25]([CH3:35])([S:31]([CH3:34])(=[O:33])=[O:32])[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:22]=1.O>O1CCOCC1.[Pd]>[F:16][C:17]1[C:18]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:19][C:20](=[O:36])[N:21]([CH2:23][CH2:24][C@@:25]([CH3:35])([S:31]([CH3:34])(=[O:32])=[O:33])[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:22]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 67249679Ethyl (2R)-4-(5-fluoro-4-iodo-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoate

Produkt 1

HCID 67248183HCID 67248183, VerbindungAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Pd EnCat™ (95 mg, 0.037 mmol) was added to a mixture of potassium carbonate (312 mg, 2.26 mmoll), phenylboronic acid (131 mg, 1.07 mmol), and ethyl (2R)-4-(5-fluoro-4-iodo-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoate (319 mg, 0.716 mmol) in dioxane:water (10 ml, 4:1) in a 20 mL vial equipped with a stir bar. The reaction was heated to 90° C. and allowed to stir overnight at that temperature. The reaction was allowed to cool to RT, filtered and the catalyst was washed with methanol (10 ml) and dichloromethane (10 ml). The filtrate was concentrated to afford a crude solid. The crude was purified via flash chromatography using an Analogix SF15-12 column and an eluant of ethyl acetate in heptane (50-100%) and methanol in ethyl acetate (0-5%) to afford the title compound as a yellowish white solid (250 mg, 64.8%). LC-MS m/z 396.1 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.23 (t, J=7.12 Hz, 3 H) 1.62 (s, 3 H) 2.15-2.32 (m, 1 H) 2.53-2.66 (m, 1 H) 3.16 (s, 3 H) 3.89-4.06 (m, 2 H) 4.07-4.26 (m, 2 H) 6.50 (d, J=7.61 Hz, 0 H) 7.20-8.12 (m, 6 H).

Aufarbeitung

  1. temperatureto cool to RT
  2. filtrationfiltered
  3. washthe catalyst was washed with methanol (10 ml) and dichloromethane (10 ml)
  4. concentrationThe filtrate was concentrated
  5. customto afford a crude solid
  6. customThe crude was purified via flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ee8c500c17204174a9d9605a5e85a8c9
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846933B2

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