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

HRID 473039Notes

Reaction equation

HRID 473039 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 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of compound 9 (90 mg, 0.19 mmol) in anhydrous toluene (10 mL) was added Lawesson's reagent (84 mg, 0.20 mmol) under a nitrogen atmosphere, the mixture was heated to 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 eluting with petroleum ether:EtOAc (3:1) to give compound 10 (65 mg, 70%) as a white solid. LC-MS tR=1.503 min in 2 min chromatography, MS (ESI) m/z 483.1 [M+H]+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto 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 eluting with petroleum ether:EtOAc (3:1)

Sources & evidence

ORD record
ord-eac934f3341641a593f783e446459118
Source dataset
uspto-grants-2014_01
Patent number
US08633212B2

Reaction notes

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