Methanol → HCID 58442313, compound

HRID 574230Notes

Reaction equation

HRID 574230 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 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).

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-0955279f0ea74fe684b3acad21fe82b7
Source dataset
uspto-grants-2015_05
Patent number
US09034879B2

Reaction notes

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