Lawesson's reagent → ethyl 2-(7-(2,5-dimethyl-1H-pyrrol-1-yl)-2-thioxo-3,4-dihydroquinolin-1(2H)-yl)propanoate

HRID 519078Notes

Reaction equation

HRID 519078 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][C:14](=O)[N:15]3[CH:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:3]([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][C:14](=[S:35])[N:15]3[CH:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86727444ethyl 2-(7-(2,5-dimethyl-1H-pyrrol-1-yl)-2-oxo-3,4-dihydroquinolin-1(2H)-yl)propanoate

Product 1

HCID 86727445ethyl 2-(7-(2,5-dimethyl-1H-pyrrol-1-yl)-2-thioxo-3,4-dihydroquinolin-1(2H)-yl)propanoateYield 12%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of ethyl 2-(7-(2,5-dimethyl-1H-pyrrol-1-yl)-2-oxo-3,4-dihydroquinolin-1(2H)-yl)propanoate (1.6 g, 4.70 mmol) and Lawesson reagent (1.9 g, 4.70 mmol) in toluene (20 mL) was heated to reflux for 2 h. The reaction mixture was cooled to ambient temperature and the mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 0-5% EtOAc in petroleum ether) to give ethyl 2-(7-(2,5-dimethyl-1H-pyrrol-1-yl)-2-thioxo-3,4-dihydroquinolin-1(2H)-yl)propanoate (0.20 g, 12%). 1H NMR (CDCl3, 400 MHz): δ 7.27 (d, J=8.0 Hz, 1H), 6.94 (d, J=8.06 Hz, 1H), 6.82 (s, 1H), 6.58 (m, 1H), 5.91 (s, 2H), 4.13 (q, J=7.2 Hz, 2H), 3.24 (m, 2H), 2.85 (m, 2H), 2.03 (s, 6H), 1.71 (d, J=7.2 Hz, 3H), 1.13 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureto reflux for 2 h
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (eluting with 0-5% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-e75f5ea35deb426796f769f9707d913b
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

Loading…