3-(4-Piperidinyl)-1H-indole → 4-bromo-3-[4-(1H-indol-3-yl)-piperidin-1-ylmethyl]-benzoic acid methyl ester

HRID 457806Notes

Reaction equation

HRID 457806 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)[NH:9][CH:8]=2)[CH2:3][CH2:2]1.[CH3:16][O:17][C:18](=[O:28])[C:19]1[CH:24]=[CH:23][C:22]([Br:25])=[C:21]([CH2:26]Br)[CH:20]=1>>[CH3:16][O:17][C:18](=[O:28])[C:19]1[CH:24]=[CH:23][C:22]([Br:25])=[C:21]([CH2:26][N:1]2[CH2:6][CH2:5][CH:4]([C:7]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[NH:9][CH:8]=3)[CH2:3][CH2:2]2)[CH:20]=1

Participants

3

Reactant 2

HCID 7022353-(4-Piperidinyl)-1H-indoleHCID 11460987Methyl 4-Bromo-3-(bromomethyl)benzoate

Product 1

HCID 694124674-bromo-3-[4-(1H-indol-3-yl)-piperidin-1-ylmethyl]-benzoic acid methyl esterYield 46%

Procedure

This compound was prepared following the procedure described in example 1 (part D) starting with 0.2 g (1 mmol) of 3-piperidin-4-yl-1H-indole and 0.39 g (1.3 mmol) 4-bromo-3-bromomethyl-benzoic acid methyl ester. After ionic exchange purification, 0.196 g (46% of yield) of 4-bromo-3-[4-(1H-indol-3-yl)-piperidin-1-ylmethyl]-benzoic acid methyl ester were obtained.

Workup

  1. customThis compound was prepared
  2. customAfter ionic exchange purification

Sources & evidence

ORD record
ord-c8dcf388c3e9421d916415cd3bb342a6
Source dataset
uspto-grants-2007_03
Patent number
US07189741B2

Reaction notes

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