Ethyl Acetate → N-(8-methyl-4H-5-oxa-1-thia-3,7-diaza-cyclopenta[a]naphthalen-2-yl)-acetamide

HRID 1807688Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1807688
Br[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[CH:4][C:3]=1[O:9][CH2:10][C:11]1[N:12]=[C:13]([NH:16][C:17](=[O:19])[CH3:18])[S:14][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].F[B-](F)(F)F.C(P(CCCC)CCCC)CCC.CCOC(C)=O>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:8][C:6]1[CH:7]=[C:2]2[C:3]([O:9][CH2:10][C:11]3[N:12]=[C:13]([NH:16][C:17](=[O:19])[CH3:18])[S:14][C:15]=32)=[CH:4][N:5]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 71317416Tributyl phosphine tetrafluoroborateHCID 86649535N-[4-(4-bromo-6-methyl-pyridin-3-yloxymethyl)-thiazol-2-yl]-acetamide

Produkt 1

HCID 86649534N-(8-methyl-4H-5-oxa-1-thia-3,7-diaza-cyclopenta[a]naphthalen-2-yl)-acetamideAusbeute 23,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

A mixture of 463 mg (1.53 mmol) N-[4-(4-bromo-6-methyl-pyridin-3-yloxymethyl)-thiazol-2-yl]-acetamide (Stage 40.3), 900 mg (2.71 mmol) cesium carbonate, 30.4 mg (0.135 mmol) palladium acetate and 81 mg (0.271 mmol) tributylphosphine tetrafluoroborate in 3 mL DMF was stirred at 115° C. for 7 h under argon. Then the reaction mixture was poured onto water, EtOAc was added and, after filtration over a layer of Hyflo Super Gel medium (Fluka 56678), the filtrate was extracted with EtOAc (2×). The combined organic layers were washed with water and brine, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to leave a residue that was purified on silica gel (=−100% EtOAc in heptane) to afford 93 mg of the title compound as a solid. LCMS: tR=0.27 min, M+H=262, M−H 260 (method J).

Aufarbeitung

  1. additionwas added
  2. filtrationafter filtration over a layer of Hyflo Super Gel medium (Fluka 56678)
  3. extractionthe filtrate was extracted with EtOAc (2×)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customto leave a residue that
  9. customwas purified on silica gel (=−100% EtOAc in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-43e8a293a40740648fd6caf581b35d73
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357707B2

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