Methyl 2-(2-chloroethoxy)benzoate → 2-(2-{4-[5-methoxy-1-(2-thiophen-3-yl-ethyl)-1H-indol-3-yl]-piperidin-1-yl}-ethoxy)-benzoic Acid

HRID 457844Notes

Reaction equation

HRID 457844 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][C:14]1[CH:18]=[CH:17][S:16][CH:15]=1)[CH:7]=[C:6]2[CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C[O:26][C:27](=[O:38])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH2:35][CH2:36]Cl>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][C:14]1[CH:18]=[CH:17][S:16][CH:15]=1)[CH:7]=[C:6]2[CH:19]1[CH2:24][CH2:23][N:22]([CH2:36][CH2:35][O:34][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[C:27]([OH:38])=[O:26])[CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 9837283Methyl 2-(2-chloroethoxy)benzoateHCID 17964293HCID 17964293, compound

Product 1

HCID 102788912-(2-{4-[5-methoxy-1-(2-thiophen-3-yl-ethyl)-1H-indol-3-yl]-piperidin-1-yl}-ethoxy)-benzoic Acid

Procedure

This compound was prepared following the procedure described in example 87 (part E) starting with 1.7 g (5 mmol) of 5-methoxy-3-piperidin-4-yl-1-(2-thiophen-3-yl-ethyl)-1H-indole and 1.2 g (5.5 mmol) of 2-(2-chloro-ethoxy)-benzoic acid methyl ester. After standard work-up and purification by flash chromatography, 0.6 g (24% of yield) of the expected acid were obtained.

Workup

  1. customThis compound was prepared
  2. customAfter standard work-up and purification

Sources & evidence

ORD record
ord-67869fc003ae446486a61a1ad477aba6
Source dataset
uspto-grants-2007_03
Patent number
US07189741B2

Reaction notes

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