Aluminum(III) Chloride → Methyl 3-[N-(4-chlorobenzyl)-5-(quinolin-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoate

HRID 327254Notes

Reaction equation

HRID 327254 reaction equation
[Cl:1][C:2]1[CH:42]=[CH:41][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)=[CH:13][CH:14]=3)[C:9](SC(C)(C)C)=[C:8]2[CH2:33][C:34]([CH3:40])([CH3:39])[C:35]([O:37][CH3:38])=[O:36])=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)=[CH:13][CH:14]=3)[CH:9]=[C:8]2[CH2:33][C:34]([CH3:39])([CH3:40])[C:35]([O:37][CH3:38])=[O:36])=[CH:41][CH:42]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 15225389Methyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-(quinolin-2-ylmethoxy)-1H-indol-2-yl)-2,2-dimethylpropanoate

Product 1

HCID 9892642Methyl 3-[N-(4-chlorobenzyl)-5-(quinolin-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 3-[N-(4-chlorobenzyl)-3-(t-butylthio)-5-(quinolin-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoate (3.77 g, 6.27 mmol) from Step D of Example 1, was dissolved in 75 mL of dry CH2Cl2 and the solution was charged with 6.27 g (47.0 mmol) of AlCl3 and the mixture was stirred at RT, under Ar, for 1.75 hours. The reaction was then quenched by the addition of 0.5N Na, K tartrate (150 mL) and the resulting mixture was extracted with EtOAc (3×). The organic extracts were washed with 0.5N Na, K tartrate (1×) and with brine (1×), and dried (MgSO4). Filtration and removal of solvents provided a brown oily residue which was chromatographed on silica gel using EtOAc-hexane (1:3) to give the title compound.

Workup

  1. customThe reaction was then quenched by the addition of 0.5N Na, K tartrate (150 mL)
  2. extractionthe resulting mixture was extracted with EtOAc (3×)
  3. washThe organic extracts were washed with 0.5N Na, K tartrate (1×) and with brine (1×)
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and removal of solvents
  6. customprovided a brown oily residue which
  7. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-b9947382f19440e1876ed686b152bd2c
Source dataset
uspto-grants-1993_12
Patent number
US05272145

Reaction notes

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