Methyl 3-(bromomethyl)benzoate → 3-[4-(1-thiophen-2-ylmethyl-1H-indol-3-yl)piperidin-1-ylmethyl]benzoic acid

HRID 457798Notes

Reaction equation

HRID 457798 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([CH2:16][C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[CH:8]=2)[CH2:3][CH2:2]1.C[O:23][C:24](=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31]Br)[CH:26]=1>>[S:18]1[CH:19]=[CH:20][CH:21]=[C:17]1[CH2:16][N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([CH:4]2[CH2:5][CH2:6][N:1]([CH2:31][C:27]3[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=3)[C:24]([OH:33])=[O:23])[CH2:2][CH2:3]2)=[CH:8]1

Participants

3

Reactant 2

HCID 517981Methyl 3-(bromomethyl)benzoateHCID 111506353-piperidin-4-yl-1-thiophen-2-ylmethyl-1H-indole

Product 1

HCID 102029963-[4-(1-thiophen-2-ylmethyl-1H-indol-3-yl)piperidin-1-ylmethyl]benzoic acidYield 176.2%

Procedure

This compound was prepared following the procedure described in example 13 (part D), starting with 4.35 mmol (15 mmol) of 3-piperidin-4-yl-1-thiophen-2-ylmethyl-1H-indole and 4.58 g (20 mmol) of 3-bromomethyl-benzoic acid methyl ester. After the standard work-up, 3.3 g of the corresponding acid was obtained. The crude mixture was purified by flash chromatography over silica gel affording 0.64 g (10% of yield) of the pure acid.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-8d8c81995e9847f1850ffc7cb2f9f7cc
Source dataset
uspto-grants-2007_03
Patent number
US07189741B2

Reaction notes

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