Water → Methyl 5-(4-t-Butylphenyldithio)-2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)-3-pyridinecarboxylate

HRID 1007238Notes

Reaction equation

HRID 1007238 reaction equation
[F:1][CH:2]([F:22])[C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([SH:17])=[C:5]([C:18]([F:21])([F:20])[F:19])[N:4]=1.[C:23]([C:27]1[CH:32]=[CH:31][C:30]([SH:33])=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24].BrBr.O>C(O)(=O)C>[C:23]([C:27]1[CH:28]=[CH:29][C:30]([S:33][S:17][C:6]2[C:7]([CH2:13][CH:14]([CH3:16])[CH3:15])=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:3]([CH:2]([F:1])[F:22])=[N:4][C:5]=2[C:18]([F:21])([F:20])[F:19])=[CH:31][CH:32]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 754544-Tert-ButylbenzenethiolHCID 9974711Methyl 2-(difluoromethyl)-4-isobutyl-5-mercapto-6-(trifluoromethyl)-3-pyridinecarboxylate

Product 1

HCID 22668800Methyl 5-(4-t-Butylphenyldithio)-2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)-3-pyridinecarboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 100 mg of compound 7 and 48.6 mg of 4-t-butylbenzenethiol in 5 ml of acetic acid was added 23 mg of bromine. The reaction mixture was stirred for 1 h, poured into water and extracted with ether. The ether extract was washed with saturated sodium bicarbonate, dried over MgSO4 and concentrated in vacuo. The residue was purified by preparative TLC (9:1 Hexane: EtOAc) on silica gel to give the desired product.

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washwas washed with saturated sodium bicarbonate
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative TLC (9:1 Hexane: EtOAc) on silica gel

Sources & evidence

ORD record
ord-66da155b6f0443a9b67bba1dbff419e3
Source dataset
uspto-grants-2004_09
Patent number
US06794396B2

Reaction notes

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