Triethylamine → Methyl 4-(2-methyl-1,3-thiazol-4-yl)-2-oxo-2H-chromene-7-carboxylate

HRID 1988214Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1988214
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13]3[N:14]=[C:15]([CH3:18])[S:16][CH:17]=3)=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C]=O>CS(C)=O.CO.CCOC(C)=O.C(Cl)Cl>[CH3:18][C:15]1[S:16][CH:17]=[C:13]([C:6]2[C:5]3[C:10](=[CH:11][C:2]([C:8]([O:9][CH3:10])=[O:12])=[CH:3][CH:4]=3)[O:9][C:8](=[O:12])[CH:7]=2)[N:14]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 598148377-bromo-4-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-oneHCID 178418416HCID 178418416, Verbindung

Produkt 1

HCID 57729247Methyl 4-(2-methyl-1,3-thiazol-4-yl)-2-oxo-2H-chromene-7-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 887MethanolLösungsmittelHCID 21226138Dichloromethane ethylacetateLösungsmittel

Versuchsvorschrift

To a solution of 7-bromo-4-(2-methyl-1,3-thiazol-4-yl)-2H-chromen-2-one (1.17 g, 3.63 mmol) in DMSO (21 ml) and methanol (12 ml) was added triethylamine (1.0 mL, 7.26 mmol) and [Pd(dppf)Cl2]2—CH2Cl2 (0.593 g, 0.73 mmol). The reaction mixture was stirred overnight at 65° C. with a balloon of carbon monoxide. After cooling to rt, the reaction mixture was diluted with EtOAc—CH2Cl2 (9:1) washed with water (3×) and brine. The organic phase was dried over MgSO4 and evaporated to dryness. The residue was purified on silica gel (hexanes-EtOAc, 8:2) to afford the title compound. 1H NMR (400 MHz, acetone-d6): δ 8.45 (m, 1H), 8.12 (s, 1H), 7.92 (m, 2H), 6.80 (s, 1H), 3.97 (s, 3H), 2.85 (s, 3H).

Aufarbeitung

  1. washwashed with water (3×) and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. customevaporated to dryness
  4. customThe residue was purified on silica gel (hexanes-EtOAc, 8:2)

Quellen und Nachweise

ORD-Eintrag
ord-ccea247173d9432094b94cefd06a3173
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07553973B2

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