Dichloromethane → Ethyl 5-chloro-3-(3,5-dimeihylphenylthio)-6-fluoroindole-2-carboxylate

HRID 50033Notes

Reaction equation

HRID 50033 reaction equation
B(F)(F)F.CCOCC.[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][C:19]=1[F:20])[NH:16][C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:14]2.[CH3:26][C:27]1[CH:28]=[C:29]([S:34]N2C(=O)CCC2=O)[CH:30]=[C:31]([CH3:33])[CH:32]=1.ClCCl>[Cl-].[Na+].O.C(Cl)(Cl)Cl>[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][C:19]=1[F:20])[NH:16][C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:14]2[S:34][C:29]1[CH:30]=[C:31]([CH3:33])[CH:32]=[C:27]([CH3:26])[CH:28]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8000Boron trifluoride etherate2×HCID 11053620N-(3,5-Dimethylphenylthio)succinimideHCID 11413806Ethyl 5-chloro-6-fluoro-1H-indole-2-carboxylate

Product 1

HCID 21301066Ethyl 5-chloro-3-(3,5-dimeihylphenylthio)-6-fluoroindole-2-carboxylateYield 102.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Boron trifluoride ethyl etherate (0.135 g, 0.12 mL, 0.001 mol) was added to a mixture of ethyl 5-chloro-6-fluoroindole-2-carboxylate (0.75 g, 0.0031 mol), N-(3,5-dimethylphenylthio)-succinimide (0.78 g, 0.0033 mol) and anhydrous dichloromethane (20 mL) under dry argon atmosphere. After stirring at room temperature for 2 hours was added boron trifluoride ethyl etherate (0.27 g, 0.24 mL, 0.002 mol) and then reaction was heated at 45° C. for 2 hours. After cooling reaction was diluted chloroform and brine while shaking. Organic layer was separated, washed with saturated solution of sodium hydrogen carbonate, then with brine and dried. The solvent was evaporated to give 1.2 g (100%) of satisfactory pure title compound, mp 170-173° C. (from ethanol).

Workup

  1. customreaction
  2. temperaturewas heated at 45° C. for 2 hours
  3. temperatureAfter cooling
  4. customreaction
  5. stirringwhile shaking
  6. customOrganic layer was separated
  7. washwashed with saturated solution of sodium hydrogen carbonate
  8. dry with materialwith brine and dried
  9. customThe solvent was evaporated

Sources & evidence

ORD record
ord-72582ea7baff4f51bacbd7e698208507
Source dataset
uspto-grants-2004_03
Patent number
US06710068B2

Reaction notes

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