Benzoyl chloride → Methyl 3-[N-(p-chlorobenzyl)-3-benzoyl-5-benzoyloxyindol-2-yl]-2,2-dimethylpropanoate

HRID 327227Notes

Reaction equation

[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[CH:9]=[C:8]2[CH2:17][C:18]([CH3:24])([CH3:23])[C:19]([O:21][CH3:22])=[O:20])=[CH:4][CH:3]=1.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCCl>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][C:27](=[O:34])[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:13][CH:14]=3)[C:9]([C:27](=[O:34])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:8]2[CH2:17][C:18]([CH3:24])([CH3:23])[C:19]([O:21][CH3:22])=[O:20])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl 3-[N-(p-chlorobenzyl)-5-hydroxy indol-2-yl]-2,2-dimethylpropanoate (609 mg) from Example 8 (Step A) was dissolved in 10 mL of 1,2-dichloroethane and the solution charged with 0.5 mL of benzoyl chloride and 680 mg of AlCl3. The reaction was heated to 80° C. under argon for 1.5 h, then quenched with 20 mL of 0.5N Na, K tartrate solution, extracted with 3×20 mL of ether, washed with 10 mL of H2O and dried (MgSO4). Removal of solvent provided an oily residue which was chromatographed on silica gel to give the title compound.

Workup

customquenched with 20 mL of 0.5N Na, K tartrate solution
extractionextracted with 3×20 mL of ether
washwashed with 10 mL of H2O
dry with materialdried (MgSO4)
customRemoval of solvent
customprovided an oily residue which
customwas chromatographed on silica gel

Sources & evidence

ORD record: ord-310dc547ee8841429e7eaa1fd5c7edf9
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05272145

Reaction notes

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