Dimethylformamide → 3-Methylcarboxy-6,7-dihydropyrido[3,2-b]thieno[2,3-d]oxepine

HRID 1949849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1949849
CO[C:3](=O)[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[C:7](I)=[N:6][CH:5]=1.CN(C)C=O.[C:25](=O)([O-:27])[O-:26].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:3][C:4]1[C:5]([C:25]([OH:27])=[O:26])=[N:6][C:7]2[C:14]3[S:15][CH:16]=[CH:17][C:13]=3[CH2:12][CH2:11][O:10][C:8]=2[CH:9]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 57900415Methyl 6-iodo-5-(2-(thiophen-3-yl)ethoxy)nicotinate

Produkt 1

HCID 668693003-Methylcarboxy-6,7-dihydropyrido[3,2-b]thieno[2,3-d]oxepineAusbeute 52,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 6-Iodo-5-(2-thiophen-3-yl-ethoxy)-nicotinic acid methyl ester (4.40 g, 11.3 mmol) in N,N-Dimethylformamide (176 mL, 2270 mmol) was added potassium carbonate (9.37 g, 67.8 mmol), triphenylphosphine (1.19 g, 4.52 mmol) and palladium acetate (508 mg, 2.26 mmol). The reaction mixture was stirred at 90° C. 8 h. The reaction mixture was diluted with MeOH then filtered through celite. The filtrate was concentrated. The crude product was purified by flash chromatography EtOAc/Hex (0-100%) (product eluted at 30%) to give 3-methylcarboxy-6,7-dihydropyrido[3,2-b]thieno[2,3-d]oxepine (52.8%). MS: (ESI+) 262.0

Aufarbeitung

  1. custom8 h
  2. filtrationthen filtered through celite
  3. concentrationThe filtrate was concentrated
  4. customThe crude product was purified by flash chromatography EtOAc/Hex (0-100%) (product eluted at 30%)

Quellen und Nachweise

ORD-Eintrag
ord-c598c3e4c4634fe8a9446b8b05f2025a
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399690B2

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