Methanol → HCID 58442313, compound

HRID 887860Notes

Reaction equation

HRID 887860 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]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 584423696-Bromo-3-(2,5-dimethyl-pyrrol-1-yl)-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester

Product 1

HCID 58442313HCID 58442313, compound

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) δ 14.42-12.61 (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

  1. customto give a suspension which
  2. customto afford a clear solution
  3. customThe solvent was removed in vacuo
  4. extractionThe mixture was extracted with EtOAc (200 ml)
  5. extractionthe organic extract
  6. dry with materialwas dried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f684b515847b4b15996cebaf33d67e76
Source dataset
uspto-grants-2012_08
Patent number
US08247436B2

Reaction notes

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