Lawesson's reagent → 1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carbothioic acid O-ethyl ester

HRID 37932Notes

Reaction equation

HRID 37932 reaction equation
[CH2:1]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[C:5]([C:15]([O:17][CH2:18][CH3:19])=O)=[CH:4][NH:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1>C1(C)C=CC=CC=1>[CH2:18]([O:17][C:15]([C:5]1[C:6]2[NH:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]=2[CH2:1][CH2:2][NH:3][CH:4]=1)=[S:29])[CH3:19]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 57467979Ethyl 1,2,3,6-tetrahydroazepino[4,5-B]indole-5-carboxylate

Product 1

HCID 865909941,2,3,6-tetrahydroazepino[4,5-b]indole-5-carbothioic acid O-ethyl esterYield 5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of ethyl 1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylate (0.51 g, 2 mmol) in toluene (20 mL) was added Lawesson's reagent (1.45 g, 3.6 mmol). The resulting suspension was heated to reflux under nitrogen for 24 hours. Solvent was evaporated to give the crude product, which was purified by column chromatography on silica gel eluting with MeOH-DCM (1:19) to give 1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carbothioic acid O-ethyl ester (27 mg); MS (ES): 273 (MH+).

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux under nitrogen for 24 hours
  3. customSolvent was evaporated
  4. customto give the crude product, which
  5. customwas purified by column chromatography on silica gel eluting with MeOH-DCM (1:19)

Sources & evidence

ORD record
ord-36b0082eb7474bf0aabe24eb3c811146
Source dataset
uspto-grants-2013_09
Patent number
US08524704B2

Reaction notes

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