Pyridine → 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 2,5-dimethyl-1H-pyrrole-1-carboxylate

HRID 1821706Notes

Reaction equation

HRID 1821706 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:7])=[CH:5][CH:6]=1.N1C=CC=CC=1.[C:14](Cl)(Cl)=[O:15].C1(C)C=CC=CC=1.[Cl:25][C:26]1[N:31]=[N:30][C:29]([O:32][C:33]2[C:38]([CH3:39])=[CH:37][CH:36]=[CH:35][C:34]=2[CH:40]2[CH2:42][CH2:41]2)=[C:28]([OH:43])[CH:27]=1>O.C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:3]([C:14]([O:43][C:28]2[CH:27]=[C:26]([Cl:25])[N:31]=[N:30][C:29]=2[O:32][C:33]2[C:38]([CH3:39])=[CH:37][CH:36]=[CH:35][C:34]=2[CH:40]2[CH2:42][CH2:41]2)=[O:15])[C:4]([CH3:7])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 1049Pyridine2×HCID 122652,5-DimethylpyrroleHCID 19083224Phosgen tolueneHCID 178424441HCID 178424441, compound

Product 1

HCID 230138946-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 2,5-dimethyl-1H-pyrrole-1-carboxylateYield 16.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

37.4 mg (0.393 mmol) of 2,5-dimethyl-1H-pyrrole was mixed with toluene (1 mL), 40.0 L (0.407 mmol) of pyridine, then 0.34 mL (0.367 mmol) of 1.08 mol/L phosgene-toluene solution were added to the mixture in an ice bath with stirring, and the resulting mixture was stirred for 1 hour. To the mixture were added 40.0 L (0.407 mmol) of pyridine, then 100 mg (0.361 mmol) of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol, and the resulting mixture was stirred for 3 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layers were combined, washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off and the obtained residue was purified by preparative thin-layer chromatography (available from MERCK CO., 1.05744, 2 plates were used, developed by hexane:ethyl acetate=2:1) to obtain 24.0 mg (0.0603 mmol, Yield: 16.7%) of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 2,5-dimethyl-1H-pyrrole-1-carboxylate (Compound No. 3630).

Workup

  1. stirringthe resulting mixture was stirred for 1 hour
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe obtained residue was purified by preparative thin-layer chromatography (available from MERCK CO., 1.05744, 2 plates were used, developed by hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-ebdb7dce3db24d8386be11d37fa340f1
Source dataset
uspto-grants-2009_10
Patent number
US07608563B2

Reaction notes

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