Dimethylformamide → Methyl 3-formyl-6-methoxy-1H-indole-2-carboxylate

HRID 40097

Reaktionsgleichung

Reaktionsgleichung von HRID 40097
O=P(Cl)(Cl)Cl.[CH3:6][O:7][C:8]([C:10]1[NH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[C:14]([O:19][CH3:20])[CH:13]=2)=[O:9].CN([CH:24]=[O:25])C>>[CH:24]([C:18]1[C:17]2[C:12](=[CH:13][C:14]([O:19][CH3:20])=[CH:15][CH:16]=2)[NH:11][C:10]=1[C:8]([O:7][CH3:6])=[O:9])=[O:25]

Komponenten

4

Edukt 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 688173Methyl-6-methoxy-2-indolecarboxylate

Produkt 1

HCID 4777855Methyl 3-formyl-6-methoxy-1H-indole-2-carboxylate

Versuchsvorschrift

General Procedure I. POCl3 (2.94 ml, 32.2 mmol) was added dropwise to anhydrous DMF (10 ml) at 0° C. under argon. After stirred for 30 min, this solution was added dropwise to a solution of methyl6-methoxy-1H-indole-2-carboxylate (Aldrich, 2.2 g, 10.7 mmol) in anhydrous DMF (20 ml) at 0° C. under argon. The reaction was stirred for 20 h at room temperature, quenched with ice, diluted with EtOAc, a precipitate formed and was filtered and washed with H2O (×3) to give the title compound as an off-white solid.

Aufarbeitung

  1. stirringThe reaction was stirred for 20 h at room temperature
  2. customquenched with ice
  3. additiondiluted with EtOAc
  4. customa precipitate formed
  5. filtrationwas filtered
  6. washwashed with H2O (×3)

Quellen und Nachweise

ORD-Eintrag
ord-d1c8310991e54dd482ed58c8c4be04ce
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524917B2

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