Formic Acid → HCID 68587830, compound

HRID 39438Notes

Reaction equation

HRID 39438 reaction equation
[CH3:1][C:2]1[C:3]([C:17]([O:19]C)=[O:18])=[CH:4][NH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([F:16])([F:15])[F:14].[OH-].[Na+].C(O)=O>CO>[CH3:1][C:2]1[C:3]([C:17]([OH:19])=[O:18])=[CH:4][NH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([F:14])([F:15])[F:16]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 67251895Methyl 4-methyl-5-(2-(trifluoromethyl)phenyl)-1H-pyrrole-3-carboxylate

Product 1

HCID 68587830HCID 68587830, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-methyl-5-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carboxylate (1.4 g, 4.9 mmol) was dissolved in methanol (12 mL), and a 5 M aqueous sodium hydroxide solution (10 mL) was added thereto, and the resulting mixture was heated under reflux for 3 hours. After the mixture was cooled to room temperature, formic acid (5 mL) was added thereto to stop the reaction. After the mixture was concentrated under reduced pressure, water (10 mL) was added thereto to suspend the resulting residue. The precipitated solid was collected by filtration and washed times with water. The obtained solid was dried under reduced pressure, whereby 4-methyl-5-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carboxylic acid (1.1 g, 83%) was obtained as a solid. The thus obtained solid was suspended in dichloromethane (10 mL), oxalyl chloride (0.86 mL, 10 mmol) was added thereto, and the resulting mixture was stirred at room temperature for 2 hours. After the mixture was concentrated under reduced pressure, the residue was dissolved in tetrahydrofuran (10 mL), and 4-(methylsulfonyl)aniline hydrochloride (1.0 g, 4.9 mmol) and N,N-diisopropylethylamine (2.8 mL, 16 mmol) were sequentially added to the solution, and the resulting mixture was heated under reflux for 18 hours. After the mixture was cooled to room temperature, the solvent was distilled off under reduced pressure, and acetonitrile (10 mL) and 3 M hydrochloric acid (100 mL) were added to the residue. A precipitated solid was triturated, collected by filtration and washed with water, and then, dried under reduced pressure, whereby 4-methyl-N-[4-(methylsulfonyl)phenyl]-5-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carboxamide (1.4 g, 89%) was obtained as a solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customthe reaction
  4. concentrationAfter the mixture was concentrated under reduced pressure, water (10 mL)
  5. additionwas added
  6. filtrationThe precipitated solid was collected by filtration
  7. washwashed times with water
  8. customThe obtained solid was dried under reduced pressure

Sources & evidence

ORD record
ord-1f6125e6eb824f4e92ee181697456c18
Source dataset
uspto-grants-2013_09
Patent number
US08524918B2

Reaction notes

Loading…