Ethyl Acetate → HCID 66765293, compound

HRID 1466795Notes

Reaction equation

HRID 1466795 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[NH:13][C:12]=2[CH3:21])[CH:5]=1.Br.Br[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O>CN(C=O)C.C1COCC1>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[N:13]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[C:12]=2[CH3:21])[CH:5]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 66765016HCID 66765016, compound

Product 1

HCID 66765293HCID 66765293, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

3-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester (0.050 g, 0.15 mmol) and 2-(bromomethyl)pyridine hydrobromide (0.049 g, 0.175 mmol) were dissolved in DMF:THF (1:1, 4 mL) and the mixture was cooled to 0° C. Cesium carbonate (0.122 g, 0.373 mmol) was added and the reaction was warmed to 90° C. for 30 minutes. The reaction as submitted to aqueous workup and silica gel chromatography (0-100% EtOAc in hexanes) to give the title compound.

Workup

  1. temperaturethe reaction was warmed to 90° C. for 30 minutes
  2. customThe reaction

Sources & evidence

ORD record
ord-c2837ac8b08a4f54a48a9848a72f1d17
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

Loading…