HCID 178418573, Verbindung → HCID 178490698, Verbindung

HRID 1888680Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1888680
[C:1]([N:5]1[CH:9]=[C:8]([CH:10]=[O:11])/[C:7](=[N:12]/[C:13](=[O:23])[C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])/[S:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:24][Mg]Br>C1COCC1>[C:1]([N:5]1[CH:9]=[C:8]([CH:10]([OH:11])[CH3:24])/[C:7](=[N:12]/[C:13](=[O:23])[C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])/[S:6]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 178418573HCID 178418573, VerbindungHCID 178490700HCID 178490700, Verbindung

Produkt 1

HCID 178490698HCID 178490698, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

The product from Example 21A (450 mg, 1.28 mmol) in THF (20 mL) was treated dropwise with methylmagnesium bromide (0.85 mL, 2.55 mmol) at −40° C. The reaction was stirred at −40° C. for 1.5 hrs, quenched with saturated NH4Cl and the mixture was extracted with EtOAc (2×). The organics were combined, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 10-80% ethyl acetate/hexane) to afford 220 mg (47%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 1.64 (d, J=6.44 Hz, 3 H) 1.67 (s, 9 H) 3.70-3.78 (m, 1 H) 3.93 (s, 3 H) 5.19 (q, J=6.44 Hz, 1 H) 6.93 (d, J=8.90 Hz, 1 H) 7.37 (dd, J=8.59, 2.76 Hz, 1 H) 7.97 (s, 1 H) 8.06 (d, J=2.76 Hz, 1 H); MS (DCI/NH4+) m/z 369 (M+H)+.

Aufarbeitung

  1. customquenched with saturated NH4Cl
  2. extractionthe mixture was extracted with EtOAc (2×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f610548baaed40b38f7498526922be5d
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501794B2

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