alpha-Bromo-o-chlorotoluene → Methyl 3-acetyl-1-(2-chlorobenzyl)-2-propylindole-6-carboxylate

HRID 1108714Notes

Reaction equation

[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:11]=2)[NH:6][C:5]=1[CH2:17][CH2:18][CH3:19])(=[O:3])[CH3:2].[H-].[Na+].[Cl:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25]Br>CN(C)C=O.C(OCC)(=O)C>[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:11]=2)[N:6]([CH2:25][C:24]2[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=2[Cl:22])[C:5]=1[CH2:17][CH2:18][CH3:19])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of methyl 3-acetyl-2-propylindole-6-carboxylate (74 mg) in dimethylformamide (1.4 ml) was added sodium hydride (60%, 15.4 mg). The mixture was stirred at 20° C. for 30 minutes, then 2-chlorobenzyl bromide (0.045 ml) was added. After stirred for 1 hour, the mixture was diluted with ethyl acetate and washed with water and brine. The organic phase was dried over sodium sulfate and evaporated in vacuo to give methyl 3-acetyl-1-(2-chlorobenzyl)-2-propylindole-6-carboxylate (125 mg) as solid.

Workup

stirringAfter stirred for 1 hour
washwashed with water and brine
dry with materialThe organic phase was dried over sodium sulfate
customevaporated in vacuo

Sources & evidence

ORD record: ord-e1d5928b9f224e6795446969d2b87036
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06069156

Reaction notes

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