Pyruvic Acid → 6-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid

HRID 1693417Notizen

Reaktionsgleichung

[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=O.[Cl:7][C:8]1[CH:13]=[C:12]([NH2:14])[C:11](I)=[CH:10][N:9]=1.C1N2CCN(CC2)C1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:7][C:8]1[N:9]=[CH:10][C:11]2[CH:4]=[C:2]([C:1]([OH:6])=[O:5])[NH:14][C:12]=2[CH:13]=1

Komponenten

Reaktionsbedingungen

Temperatur: 145 °C

Versuchsvorschrift

Pyruvic acid (0.86 ml, 12.4 mmol) was added to a solution of 2-chloro-5-iodo-pyridin-4-ylamine (Preparation 115, 1.05 mg, 4.13 mmol), palladium acetate (56 mg, 0.25 mmol) and DABCO (1.39 g, 12.4 mmol) in anhydrous DMF (30 ml). The reaction mixture was degassed with argon for 20 min, then heated to 145° C. for 2 h. The solvent was removed in vacuo and the residue taken up in water (200 mL). The suspension was made alkaline (pH 9-10) with dilute NaOH solution (1M) and filtered through Celite. After washing of the filtrate with ethyl acetate (50 mL) and ether (50 mL) the pH was adjusted to 3 with dilute HCl solution (1M). Extraction with ethyl acetate (5×50 mL), drying of the combined extracts (MgSO4) and concentration gave the title compound.

Aufarbeitung

customThe reaction mixture was degassed with argon for 20 min
customThe solvent was removed in vacuo
filtrationfiltered through Celite
washAfter washing of the filtrate with ethyl acetate (50 mL) and ether (50 mL) the pH
extractionExtraction with ethyl acetate (5×50 mL)
dry with materialdrying of the combined extracts (MgSO4) and concentration

Quellen und Nachweise

ORD-Eintrag: ord-a387d6269c6048dd8243d2a5f2b801e3
Quelldatensatz: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08158622B2

Notizen zur Reaktion

Wird geladen…