2-Chloro-5-(chloromethyl)thiophene → 4-[1-(5-chloro-thiophen-2-ylmethyl)-5-methoxy-1H-indol-3-yl]-piperidine-1-carboxylic acid ethyl ester

HRID 457867

Reaction equation

HRID 457867 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]=[C:18]([O:21][CH3:22])[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[Cl:23][C:24]1[S:25][C:26]([CH2:29]Cl)=[CH:27][CH:28]=1>>[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]=[C:18]([O:21][CH3:22])[CH:19]=3)[N:14]([CH2:29][C:26]3[S:25][C:24]([Cl:23])=[CH:28][CH:27]=3)[CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 5830792-Chloro-5-(chloromethyl)thiopheneHCID 113356564-(5-methoxy-1H-indol-3-yl)-piperidine-1-carboxylic acid ethyl ester

Product 1

HCID 694119854-[1-(5-chloro-thiophen-2-ylmethyl)-5-methoxy-1H-indol-3-yl]-piperidine-1-carboxylic acid ethyl esterYield 44%

Procedure

This compound was prepared following the procedure described in example 13 (part B) at room temperature for 15 hours, starting with 0.1 g (0.33 mmol) of 4-(5-methoxy-1H-indol-3-yl)-piperidine-1-carboxylic acid ethyl ester and 0.052 mL (0.43 mmol) of 2-chloro-5-chloromethyl-thiophene. After standard work-up, 0.06 g (44% of yield) of 4-[1-(5-chloro-thiophen-2-ylmethyl)-5-methoxy-1H-indol-3-yl]-piperidine-1-carboxylic acid ethyl ester were obtained.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-9f4ec9debecd4cbbae61f69d63e5ce31
Source dataset
uspto-grants-2007_03
Patent number
US07189741B2

Linked notes

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