Lawesson's reagent → Ethyl 6'-bromo-4-methoxy-1'-(2-(trimethylsilyl)ethylsulfonamido)-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-carboxylate

HRID 473036Notes

Reaction equation

HRID 473036 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:30][CH2:29][CH:28]([O:31][CH3:32])[CH2:27][CH2:26]3)[C:8]2([NH:16][S:17]([CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])(=[O:19])=[O:18])[C:11]([O:13][CH2:14][CH3:15])=C)=[CH:4][CH:3]=1.C[O:34]C1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:30][CH2:29][CH:28]([O:31][CH3:32])[CH2:27][CH2:26]3)[C:8]2([NH:16][S:17]([CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])(=[O:18])=[O:19])[C:11]([O:13][CH2:14][CH3:15])=[O:34])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 67043662N-(6'-bromo-1'-(1-ethoxyvinyl)-4-methoxy-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-yl)-2-(trimethylsilyl)ethanesulfonamide

Product 1

HCID 67043624Ethyl 6'-bromo-4-methoxy-1'-(2-(trimethylsilyl)ethylsulfonamido)-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-carboxylateYield 73%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of compound 9 (40 mg, 0.090 mmol) in anhydrous toluene (5 mL) was added Lawesson's reagent (40 mg, 0.099 mmol) under a nitrogen atmosphere, the mixture was heated at reflux for 12 h. After cooling down, the solvent was removed by evaporation in vacuo and the resulting residue was purified by column chromatography on silica gel (petroleum ether:EtOAc=3:1) to give compound 10 (30 mg, 73%) as a white solid. LC-MS tR=1.420 min in 2 min chromatography, MS (ESI) m/z 459.1 [M+H]+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 12 h
  3. temperatureAfter cooling down
  4. customthe solvent was removed by evaporation in vacuo
  5. customthe resulting residue was purified by column chromatography on silica gel (petroleum ether:EtOAc=3:1)

Sources & evidence

ORD record
ord-3622ad8517d54d70850a7e501b6c20a0
Source dataset
uspto-grants-2014_01
Patent number
US08633212B2

Reaction notes

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