HCID 10860687, compound → HCID 90281410, compound

HRID 1471633Notes

Reaction equation

HRID 1471633 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:5]1[CH2:19]Br)(=[O:3])[CH3:2].[C:21](=[S:24])([O-:23])[CH3:22].[K+]>CC(C)=O.CCOC(C)=O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:5]1[CH2:19][S:24][C:21](=[O:23])[CH3:22])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 10860687HCID 10860687, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 90281410HCID 90281410, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2-(1-acetyl-2-(bromomethyl)-1H-indol-3-yl)acetate (I-4A, 640 mg, 1.9 mmol) in acetone (10 ml) was added potassium ethanethioate (1.3 g, 11.2 mmol). The solution was heated at reflux for 1 hour. The solution was cooled and then diluted with EtOAc (50 ml) and washed with NaHCO3 (aq) (2×25 ml). The organic layer was dried with Na2SO4, filtered and concentrated. The crude product was introduced to a silica gel loading column and purified by column chromatography (10-30 EtOAc/hexanes) to get 533 mg (1.6 mmol, 84%) product. MS (m/z) 334 [M+H]+.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 1 hour
  3. temperatureThe solution was cooled
  4. washwashed with NaHCO3 (aq) (2×25 ml)
  5. dry with materialThe organic layer was dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. additionThe crude product was introduced to a silica gel loading column
  9. custompurified by column chromatography (10-30 EtOAc/hexanes)

Sources & evidence

ORD record
ord-4c8d8c92b3ac406abbfb0813a7f2fd31
Source dataset
uspto-grants-2015_04
Patent number
US09012441B2

Reaction notes

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