Ammonium formate → HCID 71657497, Verbindung

Reaktionsgleichung

[CH2:1]([O:3][C:4](=[O:34])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:15]2=[N:16][C:17]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)[N:19]=[C:14]2[CH:13]=[CH:12]1)[CH3:2].C([O-])=O.[NH4+]>CCO.[Pd]>[C:23]1([CH3:26])[CH:22]=[CH:21][C:20]([C:18]2[N:19]=[C:14]3[CH2:13][CH2:12][N:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:34])[C:15]3=[N:16][C:17]=2[C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)=[CH:25][CH:24]=1

Komponenten

Versuchsvorschrift

7-(2,3-Di-p-tolyl-pyrrolo[2,3-b]pyrazin-5-yl)-heptanoic acid ethyl ester (Intermediate B) (35 mg, 0.077 mmol) in dry EtOH (1 ml) under nitrogen at RT was treated with ammonium formate (24.22 mg, 0.384 mmol) followed by Pd on carbon (8.18 mg, 7.68 μmol). The resulting black suspension was heated at reflux for 16 hours, overnight. The reaction mixture was cooled to RT and then loaded onto a Celite® (filter material) column. The column was eluted with 1:1 MeOH/DCM and the filtrate concentrated under reduced pressure. The resultant residue was dissolved in DCM (50 ml), washed with water (×2) and the organic solvent removed under reduced pressure. Purification by chromatography on silica eluting with 0-30% EtOAc in iso-hexane afforded the titled compound;