Potassium Carbonate → (3-Bromo-quinolin-6-yloxy)-methylsulfanyl-acetic acid methyl ester
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([OH:12])=[CH:7][CH:6]=2.[CH3:13][O:14][C:15](=[O:20])[CH:16](Cl)[S:17][CH3:18].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH3:13][O:14][C:15](=[O:20])[CH:16]([O:12][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]=[CH:3][C:2]([Br:1])=[CH:11]2)[S:17][CH3:18]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
3-Bromo-quinolin-6-ol (17.47 g) (preparation described in Liebigs Ann Chem., 1966, 98-106), was dissolved in dry DMF (150 ml). Chloro-methylsulfanyl-acetic acid methyl ester (18.07 g) and dry potassium carbonate (43.12 g) were added at room temperature (rt). The resulting suspension was stirred for 2 hours after which time the reaction mixture was diluted with ethyl acetate and poured onto sat. sodium hydrogen carbonate (200 ml). The two phases were separated and the aqueous layer was extracted three times with ethyl acetate (3×200 ml). The combined organic layers were dried over magnesium sulphate, filtered and evaporated. The residue was purified by column chromatography (heptane/ethyl acetate 7:3) to provide (3-bromo-quinolin-6-yloxy)-methylsulfanyl-acetic acid methyl ester as yellowish solid (24 g).
Workup
- customThe two phases were separated
- extractionthe aqueous layer was extracted three times with ethyl acetate (3×200 ml)
- dry with materialThe combined organic layers were dried over magnesium sulphate
- filtrationfiltered
- customevaporated
- customThe residue was purified by column chromatography (heptane/ethyl acetate 7:3)
Sources & evidence
- ORD record
- ord-1104d866e72247e3bd9b8656692a347a
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507509B2
Reaction notes
Loading…