3-(Bromomethyl)thiophene → 4-(1-thiophen-3-ylmethyl-1H-indol-3-yl)-piperidine-1-carboxylic acid ethyl ester

HRID 457864Notes

Reaction equation

HRID 457864 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].Br[CH2:22][C:23]1[CH:27]=[CH:26][S:25][CH:24]=1>C(OCC)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:22][C:23]3[CH:27]=[CH:26][S:25][CH:24]=3)[CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 5207033-(Bromomethyl)thiopheneHCID 11380267Ethyl 4-(1H-indol-3-yl)piperidine-1-carboxylate

Product 1

HCID 694131844-(1-thiophen-3-ylmethyl-1H-indol-3-yl)-piperidine-1-carboxylic acid ethyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

This compound was prepared following the procedure described in example 13 (part B) at room temperature for 15 hours, starting with 0.2 g (0.73 mmol) of 4-(1H-indol-3-yl)-piperidine-1-carboxylic acid ethyl ester and 1.64 mL (0.95 mmol) of a freshly prepared 0.6 M solution of 3-bromomethylthiophene in ethyl ether. After standard work-up, 0.27 g (100% of yield) of 4-(1-thiophen-3-ylmethyl-1H-indol-3-yl)-piperidine-1-carboxylic acid ethyl ester were obtained.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-a6d5d601be254f6abfedac8230864914
Source dataset
uspto-grants-2007_03
Patent number
US07189741B2

Reaction notes

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