Sodium Hydroxide → 3-(2,5-Dimethyl-pyrrol-1-yl)-5,6-bis-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]([C:22]([F:25])([F:24])[F:23])[N:6]=1)=[O:4].[OH-].[Na+]>CO>[CH3:16][C:15]1[N:11]([C:10]2[C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]([C:22]([F:25])([F:23])[F:24])=[C:8]([C:18]([F:19])([F:20])[F:21])[CH:9]=2)[C:12]([CH3:17])=[CH:13][CH:14]=1Participants
Procedure
To a stirred solution 3-(2,5-dimethyl-pyrrol-1-yl)-5,6-bis-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (1.28 g, 3.49 mmol) in methanol (25 ml) was added 1M NaOH (7 ml, 6.99 mmol) and the reaction mixture was left to stir at RT for 30 min. The solvent was removed in vacuo and water (20 ml) was added to the remaining residue. The pH was adjusted to pH 4/5 by the addition of 1M HCl. The mixture was extracted with EtOAc (3×20 ml) and the combined organic extracts were washed with brine (30 ml), dried (MgSO4) and concentrated in vacuo and dried in a vacuum oven (50° C.) overnight to give the crude title product as an orange solid which was used without further purification; LC-MS: Rt 1.23 min; MS m/z 353.1 [M+H]+; Method 2minLC_v003.
Workup
- waitthe reaction mixture was left
- customThe solvent was removed in vacuo and water (20 ml)
- additionwas added to the remaining residue
- additionThe pH was adjusted to pH 4/5 by the addition of 1M HCl
- extractionThe mixture was extracted with EtOAc (3×20 ml)
- washthe combined organic extracts were washed with brine (30 ml)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customdried in a vacuum oven (50° C.) overnight
Sources & evidence
- ORD record
- ord-c663d09ff34148a3818c533fdb72fbc3
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365552B2
Reaction notes
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