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

HRID 1503465Notes

Reaction equation

HRID 1503465 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:27][CH2:26][CH:25]([O:28][CH3:29])[CH2:24][CH2:23]3)[C:8]2([NH:16][S:17]([C:19]([CH3:22])([CH3:21])[CH3:20])=[O:18])[C:11]([O:13][CH2:14][CH3:15])=C)=[CH:4][CH:3]=1.C[O:31]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([CH2:27][CH2:26][CH:25]([O:28][CH3:29])[CH2:24][CH2:23]3)[C:8]2([NH:16][S:17]([C:19]([CH3:21])([CH3:22])[CH3:20])=[O:18])[C:11]([O:13][CH2:14][CH3:15])=[O:31])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 58198087N-(6'-bromo-1'-(1-ethoxyvinyl)-4-methoxy-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-yl)-2-methylpropane-2-sulfinamide

Product 1

HCID 58197767Ethyl 6'-bromo-1'-(1,1-dimethylethylsulfinamido)-4-methoxy-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-carboxylateYield 25%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 8 mL vial was charged with compound 5 (130 mg, 0.316 mmol) and Lawesson's reagent (138 mg, 0.342 mmol). Toluene (2 mL) was added, and the vial was sealed and placed into CEM microwave reactor and irradiated at 140° C. for 1 h. After cooling down, the solvent was removed by evaporation in vacuo and the resulting residue was purified by column chromatography over silica gel (petroleum ether:EtOAc, 50:1 to 10:1) to give compound 6 (35 mg, 25%) as a whit solid. LC-MS tR=1.244 min in 2 min chromatography, MS (ESI) m/z=435.2 [M+H]+.

Workup

  1. customthe vial was sealed
  2. customirradiated at 140° C. for 1 h
  3. temperatureAfter cooling down
  4. customthe solvent was removed by evaporation in vacuo
  5. customthe resulting residue was purified by column chromatography over silica gel (petroleum ether:EtOAc, 50:1 to 10:1)

Sources & evidence

ORD record
ord-b30d8b69d17f4c1d996d7c2fdbee8734
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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