Water → 2-(4-Fluorophenyl)-3-(pyridin-4-yl)-4-(2,4,6-trifluorobenzoylaminomethyl)-1H-pyrrole

HRID 1244986Notes

Reaction equation

HRID 1244986 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[C:10]=1[C:11](Cl)=[O:12].Cl.Cl.[NH2:22][CH2:23][C:24]1[C:25]([C:36]2[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=2)=[C:26]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[NH:27][CH:28]=1.O>O1CCCC1>[F:35][C:32]1[CH:31]=[CH:30][C:29]([C:26]2[NH:27][CH:28]=[C:24]([CH2:23][NH:22][C:11](=[O:12])[C:10]3[C:9]([F:8])=[CH:17][C:16]([F:18])=[CH:15][C:14]=3[F:19])[C:25]=2[C:36]2[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=2)=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 1448952,4,6-Trifluorobenzoyl chlorideHCID 219227564-Aminomethyl-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole Dihydrochloride

Product 1

HCID 219228152-(4-Fluorophenyl)-3-(pyridin-4-yl)-4-(2,4,6-trifluorobenzoylaminomethyl)-1H-pyrroleYield 38.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

265 μl (1.905 mmol) of triethylamine and 96 mg (0.493 mmol) of 2,4,6-trifluorobenzoyl chloride were added to a suspension of 162 mg (0.476 mmol) of 4-aminomethyl-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole dihydrochloride [prepared as described in Example 5 above] in 3.3 ml of tetrahydrofuran. The resulting mixture was stirred at room temperature for 4 hours. At the end of this time, water was added to the reaction mixture and then this was extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous sodium sulfate and then concentrated by evaporation under reduced pressure. The residue thus obtained was washed with diethylether to give 78 mg (yield 38%) of the title compound as a pale yellow powder.

Workup

  1. extractionthis was extracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe residue thus obtained
  7. washwas washed with diethylether

Sources & evidence

ORD record
ord-3c9ae1676760426786d0f50d0fce1738
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

Loading…