Methyl Benzoate → HCID 86685704, compound

HRID 1844638Notes

Reaction equation

HRID 1844638 reaction equation
[CH3:1][O:2][C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:11][C:12]([F:30])([F:29])[C:13]1[CH:18]=[C:17]([C:19]([C:21]([F:24])([F:23])[F:22])=[CH2:20])[CH:16]=[C:15]([C:25]([F:28])([F:27])[F:26])[CH:14]=1.[F-].[CH2:32]([N+:36](CCCC)(CCCC)CCCC)[CH2:33]CC.[CH2:49]1COCC1>>[CH3:1][O:2][C:3](=[O:10])[C:4]1[CH:9]=[CH:8][C:7]([CH:32]2[CH2:33][C:19]([C:17]3[CH:18]=[C:13]([C:12]([F:29])([F:30])[F:11])[CH:14]=[C:15]([C:25]([F:28])([F:27])[F:26])[CH:16]=3)([C:21]([F:22])([F:23])[F:24])[CH:20]=[N:36]2)=[CH:6][C:5]=1[CH3:49]

Participants

5

Reactant 4

HCID 7150Methyl BenzoateHCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 498208821,3-Bis(trifluoromethyl)-5-(1,1,1-trifluoroprop-2-en-2-yl)benzene

Product 1

HCID 86685704HCID 86685704, compound

Procedure

To a solution of 2-methyl-4-(methylsulfanyl-trimethylsilanylmethylimino]-methyl)-benzoic acid methyl ester (Example 19) (135 mg) and 1,3-bis-trifluoromethyl-5-(1-trifluoromethyl-vinyl)-benzene (see WO 2007125984) (179 mg) in THF (5 ml) was added at 5° C. tetrabutylammonium fluoride (TBAF) (0.11 ml, 1M in THF). The reaction mixture was stirred at ambient temperature for 5 hours. The reaction mixture was filtered over silica and concentrated. The residue was purified by preparative HPLC to give 4-[4-(3,5-bis-trifluoromethyl-phenyl)-4-trifluoromethyl-3,4-dihydro-2H-pyrrol-2-yl]-2-methyl-benzoic acid methyl ester (124 mg). 1H-NMR (400 MHz, CDCl3): 8.60-7.70 (m, 6H), 5.03 (d, 1H), 4.52 (d, 1H), 3.98-3.90 (m, 4H), 3.55-3.40 (m, 1H), 2.68 (s, 3H) ppm.

Workup

  1. filtrationThe reaction mixture was filtered over silica
  2. concentrationconcentrated
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-7282cecec3f94baebeb1a4df430430ea
Source dataset
uspto-grants-2015_02
Patent number
US08946447B2

Reaction notes

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