Lawesson's reagent → 4-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-3-methylbutanethioamide

HRID 1684016Notes

Reaction equation

HRID 1684016 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][CH:19]([CH3:24])[CH2:20][C:21]([NH2:23])=O)=[C:8]2[CH3:25])=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:37])=CC=1>O1CCOCC1>[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][CH:19]([CH3:24])[CH2:20][C:21](=[S:37])[NH2:23])=[C:8]2[CH3:25])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 190416504-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-3-methylbutanamide

Product 1

HCID 190417254-[1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-3-methylbutanethioamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the amide (530 mg, 1.30 mmol) of Example 90 in 1,4-dioxane (10.0 mL) was added the Lawesson reagent (310 mg, 0.767 mmol). After refluxing for 2 min, the solvent was evaporated in vacuo and the title product was purified by flash chromatography (30% EtOAc in hexane).

Workup

  1. temperatureAfter refluxing for 2 min
  2. customthe solvent was evaporated in vacuo
  3. customthe title product was purified by flash chromatography (30% EtOAc in hexane)

Sources & evidence

ORD record
ord-91a6c27577af4eaba46538f7760c50aa
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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