Methanol → 3-(2,5-Dimethyl-pyrrol-1-yl)-6-methoxy-5-trifluoromethyl-pyridine-2-carboxylic acid
Reaktionsgleichung
C[O:2][C:3]([C:5]1[C:10]([N:11]2[C:15]([CH3:16])=[CH:14][CH:13]=[C:12]2[CH3:17])=[CH:9][C:8]([C:18]([F:21])([F:20])[F:19])=[C:7](Br)[N:6]=1)=[O:4].[OH-:23].[Na+].[CH3:25]O>>[CH3:17][C:12]1[N:11]([C:10]2[C:5]([C:3]([OH:2])=[O:4])=[N:6][C:7]([O:23][CH3:25])=[C:8]([C:18]([F:19])([F:20])[F:21])[CH:9]=2)[C:15]([CH3:16])=[CH:14][CH:13]=1Komponenten
4
Versuchsvorschrift
6-Bromo-3-(2,5-dimethyl-pyrrol-1-yl)-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (2 g, 5.30 mmol) was dissolved in MeOH (40 ml) and treated with 2M NaOH (20 ml) to give a suspension which was stirred at RT for 1 hr to afford a clear solution. The solvent was removed in vacuo and the residue was acidified to pH1 with 5M HCl. The mixture was extracted with EtOAc (200 ml) and the organic extract was dried (MgSO4) and concentrated in vacuo to afford the title compound as a dark brown solid which was used in the next step without further purification; LC_MS Rt=1.50 min [M+H]+ 315.2.1/316.2 (Method 2minLC_v002); 1H NMR (400 MHz, DMSO-d6) δ14.42-12.61 (COOH, b hump), 8.25 (1H, s), 5.84 (2H, s), 4.13 (3H, s), 1.97 (6H, s); 19F NMR (400 MHz, DMSO-d6) δ −62.43 (CF3, s).