Cesium carbonate → ethyl-2-{1-[2-(dimethylamino)ethyl]-1H-indol-3-yl}-2-oxoacetate

HRID 1472936Notes

Reaction equation

HRID 1472936 reaction equation
ClC[CH2:3][CH2:4][N:5]([CH3:7])[CH3:6].[CH2:8]([O:10][C:11](=[O:23])[C:12]([C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)=[O:13])[CH3:9].C([O-])([O-])=O.[Cs+].[Cs+]>>[CH2:8]([O:10][C:11](=[O:23])[C:12]([C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]([CH2:3][CH2:4][N:5]([CH3:7])[CH3:6])[CH:15]=1)=[O:13])[CH3:9]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 101242Ethyl 3-indolylglyoxylate

Product 1

HCID 67255053ethyl-2-{1-[2-(dimethylamino)ethyl]-1H-indol-3-yl}-2-oxoacetateYield 63.3%

Procedure

The general procedure 1 was then followed using 1-chloro-3-dimethylaminopropane (7 mmol, 0.75 g), ethyl-2-(1H-indol-3-yl)-2-oxoacetate (6 mmol, 1.3 g) and Cs2CO3 (6.6 mmol, 2.15 g). The purification was achieved by column chromatography (petro-lether:ethylacetate:diethylamine 6:3:1) to yield ethyl-2-{1-[2-(dimethylamino)ethyl]-1H-indol-3-yl}-2-oxoacetate (3.8 mmol, 63%) as an pale yellow oil. IR {tilde over (ν)} [cm−1]=3023; 2962; 2917; 1732; 1630. EI-MS m/z (rel. int.)=302 (8.21%; M+•.). 1H NMR (300 MHz, CDCl3) 8.43 (m; 1H; indole-H); 8.39 (s; 1H; indole-H); 7.33 (m; 3H; indole-H); 4.40 (q; 3J=7.1 Hz; 2H; OCH2CH3); 4.27 (t; 3J=6.8 Hz; 2H; indole-CH2CH2CH2N); 2.22 (s; 6H; N(CH3)2); 2.20 (m; 2H; indole-CH2CH2CH2N); 2.00 (quint; 3J=6.7 Hz; 2H; indole-CH2CH2CH2N); 1.42 (t; 3J=7.1 Hz; 3H OCH2CH3).

Workup

  1. customThe purification

Sources & evidence

ORD record
ord-70903f80ad0e4a3fbed3014bf447889c
Source dataset
uspto-grants-2015_04
Patent number
US09012659B2

Reaction notes

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