Boron trifluoride etherate → ethyl 5-chloro-3-(phenylthio)-1H-indole-2-carboxylate

HRID 260477

Reaction equation

HRID 260477 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.[C:16]1([S:22]N2C(=O)CCC2=O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.B(F)(F)F.CCOCC>C(Cl)Cl.C(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>[C:16]1([S:22][C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=3)[NH:7][C:6]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 8000Boron trifluoride etherateHCID 78518Ethyl 5-chloroindole-2-carboxylateHCID 361774NSC625040

Product 1

HCID 15035363ethyl 5-chloro-3-(phenylthio)-1H-indole-2-carboxylate

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a partial suspension of ethyl 5-chloroindole-2-carboxylate (698 mg, 3.1 mmol) and N-(phenylthio)succinimide (683 mg, 3.3 mmol) in anhydrous methylene chloride (20 mL) at ambient temperature under an inert gas atmosphere was added boron trifluoride etherate (0.12 mL, 1.0 mmol). The reaction was monitored by tlc (thin layer chromatography) until complete. After 2 hours, the reaction was diluted with chloroform and neutralized with aq. NaHCO3. The organic layer was dried (Na2SO4), filtered through a pad of charcoal, and the solvents evaporated. The residue was triturated with hexanes as the product crystallized out to yield the title product, mp 160°-162° C. [see Table II, mp 163°-164° C⟧ This material was used as is.

Workup

  1. dry with materialThe organic layer was dried (Na2SO4)
  2. filtrationfiltered through a pad of charcoal
  3. customthe solvents evaporated
  4. customThe residue was triturated with hexanes as the product
  5. customcrystallized out

Sources & evidence

ORD record
ord-d888f10c1e12454e8ddab9396b718edd
Source dataset
uspto-grants-1996_06
Patent number
US05527819

Linked notes

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