Methanol → 3-(2,5-Dimethyl-pyrrol-1-yl)-6-methoxy-5-trifluoromethyl-pyridine-2-carboxylic acid
Reaction equation
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]=1Participants
Procedure
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 h to afford a clear solution. The solvent was removed in vacuo and the resulting 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), 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).
Workup
- customto give a suspension which
- customto afford a clear solution
- customThe solvent was removed in vacuo
- extractionThe mixture was extracted with EtOAc (200 ml)
- extractionthe organic extract
- dry with materialwas dried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-10720694511d455f8809e838127c981d
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365552B2
Reaction notes
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