Ethyl 5-(4-(tert-butyl)phenyl)-1H-indole-2-carboxylate → 5-(4-tert-Butylphenyl)-1-(4-(2-methyl-1-(4-methylpiperazin-1-yl)-1-oxopropan-2-yloxy)phenyl)indole-2-carboxylic acid hydrochloride

HRID 646128Notes

Reaction equation

HRID 646128 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=1)=[CH:10][CH:9]=2)=[O:5])C.[ClH:25].Br[C:27]1[CH:45]=[CH:44][C:30]([O:31][C:32]([CH3:43])([CH3:42])[C:33]([N:35]2[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]2)=[O:34])=[CH:29][CH:28]=1>>[ClH:25].[C:21]([C:18]1[CH:17]=[CH:16][C:15]([C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[N:7]([C:27]2[CH:45]=[CH:44][C:30]([O:31][C:32]([CH3:43])([CH3:42])[C:33]([N:35]4[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]4)=[O:34])=[CH:29][CH:28]=2)[C:6]([C:4]([OH:5])=[O:3])=[CH:14]3)=[CH:20][CH:19]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

3

Reactant 2

HCID 68475095Ethyl 5-(4-(tert-butyl)phenyl)-1H-indole-2-carboxylateHCID 686975001-(2-(4-Bromophenoxy)-2-methylpropanoyl)-4-methylpiperazine hydrochloride

Product 1

HCID 686972965-(4-tert-Butylphenyl)-1-(4-(2-methyl-1-(4-methylpiperazin-1-yl)-1-oxopropan-2-yloxy)phenyl)indole-2-carboxylic acid hydrochloride

Procedure

The title compound was prepared in accordance with Example 1 using 5-(4-tert-butylphenyl)indole-2-carboxylic acid ethyl ester and 1-(2-(4-bromophenoxy)-2-methylpropanoyl)-4-methylpiperazine hydrochloride (see (a)), followed by precipitation of the hydrochloride salt using HCl (4 M in dioxane).

Workup

  1. customfollowed by precipitation of the hydrochloride salt

Sources & evidence

ORD record
ord-66bb25cfd454418f81a37bc14649eee9
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

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