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Water → 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-methyl-N-thietan-3-yl-benzamide

HRID 1844646
Notes
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Reaction equation

HRID 1844646 reaction equation
CS[C:3](=[N:18][CH2:19][Si](C)(C)C)[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:16])[NH:11][CH:12]2[CH2:15][S:14][CH2:13]2)=[C:6]([CH3:17])[CH:5]=1.[Cl:24][C:25]1[CH:30]=[C:29]([C:31]([C:33]([F:36])([F:35])[F:34])=[CH2:32])[CH:28]=[C:27]([Cl:37])[CH:26]=1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[Cl:24][C:25]1[CH:30]=[C:29]([C:31]2([C:33]([F:36])([F:34])[F:35])[CH2:19][N:18]=[C:3]([C:4]3[CH:9]=[CH:8][C:7]([C:10]([NH:11][CH:12]4[CH2:15][S:14][CH2:13]4)=[O:16])=[C:6]([CH3:17])[CH:5]=3)[CH2:32]2)[CH:28]=[C:27]([Cl:37])[CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 675060713-methyl-4-(thietan-3-ylcarbamoyl)-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester

Product 1

HCID 666553094-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-methyl-N-thietan-3-yl-benzamide
Yield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-methyl-4-(thietan-3-ylcarbamoyl)-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester (Example I19) (16 mg) and 1,3-dichloro-5-(1-trifluoromethyl-vinyl)-benzene (see WO 2007/125984) (12 mg) in THF (2 ml) was added at −5° C. tetrabutylammonium fluoride trihydrate (TBAF) (0.41 g) dissolved in THF (1.5 ml). The reaction mixture was stirred at ambient temperature for 16 hours. Water was added and the mixture was extracted twice with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (eluent: ethyl acetate/heptanes 1:2) to give 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-methyl-N-thietan-3-yl-benzamide (20 mg). 1H-NMR (400 MHz, CDCl3): 7.75-7.25 (m, 6H), 6.30 (s, 1H), 5.45 (m, 1H), 4.90 (d, 1H), 4.45 (d, 1H), 3.82 (d, 1H), 3.55-3.38 (m, 5H), 2.48 (s, 3H) ppm.

Workup

  1. customwas added at −5° C.
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel (eluent: ethyl acetate/heptanes 1:2)

Sources & evidence

ORD record
ord-2bdaab1973c043679012a13b8dca2c26
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946447B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes