Sodium methanethiolate → HCID 89924118, compound

HRID 1500932Notes

Reaction equation

HRID 1500932 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[CH:7]=[C:6]1[C:15]([O:17][CH2:18][CH3:19])=[O:16].[CH3:20][S-:21].[Na+]>CCO>[Cl:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([CH2:4][CH2:3][CH2:2][S:21][CH3:20])[C:6]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7]2

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 89924264HCID 89924264, compound

Product 1

HCID 89924118HCID 89924118, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 1-(3-bromopropyl)-5-chloro-1H-indole-2-carboxylate (38.5 g, 0.112 mol) and sodium methanethiolate (9.4 g, 0.135 mol) in 500 mL of EtOH was stirred at RT for 16 hours. The mixture was concentrated in vacuo and the residue was diluted with 200 mL of water and then extracted with EtOAc (100 mL×2). The combined organic layers were washed with 100 mL of brine and 100 mL of water, and then dried over Na2SO4 and concentrated in vacuo to afford 34.1 g of the crude ethyl 5-chloro-1-[3-(methylsulfanyl)propyl]-1H-indole-2-carboxylate, which was used without further purification.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue was diluted with 200 mL of water
  3. extractionextracted with EtOAc (100 mL×2)
  4. washThe combined organic layers were washed with 100 mL of brine and 100 mL of water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4298bd0ca70249cdb881b5549a7e6a9c
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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