Water → HCID 57500672, Verbindung

HRID 1919654Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1919654
Br[C:2]1[S:6][CH:5]=[N:4][C:3]=1[C:7]([O:9]C)=O.Cl.N[C:13]1[C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O.C([O-])(=O)C.[Na+].O.C[N:33](C=O)C>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]>[O:9]=[C:7]1[C:3]2[N:4]=[CH:5][S:6][C:2]=2[C:15]2[CH:16]=[CH:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:13][C:14]=2[NH:33]1

Komponenten

7

Edukt 5

HCID 962WaterHCID 6228DimethylformamideHCID 517045Sodium AcetateHCID 40787018Methyl 5-bromo-1,3-thiazole-4-carboxylateHCID 67039410HCID 67039410, Verbindung

Produkt 1

HCID 57500672HCID 57500672, VerbindungAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

In a microwave vessel, methyl 5-bromothiazole-4-carboxylate (1.0 eq, 97 mg, 0.44 mmol), 2-amino-3-methoxycarbonyl phenyl boronic acid HCl (1.1 eq, 111 mg, 0.48 mmol), sodium acetate (3.0 eq, 107 mg, 1.31 mmol) and PdCl2(dppf) (0.05 eq, 11 mg, 0.022 mmol) were mixed together in anhydrous DMF (1 ml). The mixture was heated in a microwave oven at 120° C. for 10 nm. Water was added and the material extracted with CH2Cl2. The combined extracts were washed with brine, dried over Na2SO4 and the solvents removed by evaporation. The material was dissolved in a mixture of CH2Cl2 and MeOH and the solution filtered through a pad of celite. Evaporation of the volatiles afforded crude methyl 4-oxo-4,5-dihydrothiazolo[4,5-c]quinoline-7-carboxylate as a black solid (44 mg, 39% yield). A small part of the compound was subjected to preparative HPLC for analytical purpose. LCMS (ES): 95% pure, m/z 261 [M+1]+.

Aufarbeitung

  1. extractionthe material extracted with CH2Cl2
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. customthe solvents removed by evaporation
  5. dissolutionThe material was dissolved in a mixture of CH2Cl2 and MeOH
  6. filtrationthe solution filtered through a pad of celite
  7. customEvaporation of the volatiles

Quellen und Nachweise

ORD-Eintrag
ord-37f6558c650444b488cbfe6f4cc6df19
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08168651B2

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