Potassium ethanethioate → HCID 58763429, compound

HRID 858290Notes

Reaction equation

HRID 858290 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([O:35][CH3:36])=[O:34])[CH:28]=2)[C:7]2[C:12]([C:13]=1[CH2:14][CH2:15]OS(C1C=CC(C)=CC=1)(=O)=O)=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4].[C:37]([O-:40])(=[S:39])[CH3:38].[K+]>CN(C=O)C.O>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([O:35][CH3:36])=[O:34])[CH:28]=2)[C:7]2[C:12]([C:13]=1[CH2:14][CH2:15][S:39][C:37](=[O:40])[CH3:38])=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4]

Participants

5

Reactant 2

HCID 23670855Potassium ethanethioateHCID 58763427HCID 58763427, compound

Product 1

HCID 58763429HCID 58763429, compoundYield 106.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(3-methoxycarbonyl-phenyl)-3-[2-(toluene-4-sulfonyloxy)-ethyl]-1H-indole-2-carboxylic acid methyl ester (0.37 g, 0.73 mmol) and potassium thioacetate (0.092 g, 0.8 mmol) in DMF (5 mL) was stirred at room temperature overnight. The reaction mixture was diluted with water and extracted with EtOAc. The organic extract was washed with saturated NaHCO3, dried over Na2SO4, and concentrated to give 0.32 g of 3-(2-acetylsulfanyl-ethyl)-1-(3-methoxycarbonyl-phenyl)-1H-indole-2-carboxylic acid methyl ester as a yellow oil (100% crude yield): 1H NMR (CDCl3, 300 MHz) δ 2.36 (s, 3H), 3.20 (q, J=6.87 Hz, 2H), 3.40 (q, J=6.87 Hz, 2H), 3.74 (s, 3H), 3.91 (s, 3H), 7.01 (d, J=7.82 Hz, 1H), 7.20–7.31 (m, 3H), 7.44 (d, J=8.02 Hz, 1H), 7.48–7.52 (m, 1H), 7.59(t, J=7.82 Hz, 1H), 7.88 (d, J=7.82 Hz, 1H), 7.97(t, J=1.53 Hz, 1H); 8.13 (dt, J=7.82, 1.34 Hz, 1H).

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with saturated NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6ea6123939a14531924afd81fc3045f1
Source dataset
uspto-grants-2006_12
Patent number
US07148250B2

Reaction notes

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