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

HRID 1094571Notes

Reaction equation

HRID 1094571 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-6ceab82fbd164f7f914a4f37aa4188f2
Source dataset
uspto-grants-2012_03
Patent number
US08133992B2

Reaction notes

Loading…