Sodium Carbonate → HCID 22598379, compound

Participants

Reaction Conditions

Reaction Steps

To 0.4 g. (1.2 mmole) of N-[6-bromo-2-(3-fluorophenyl)4-quinolinyl]-N-methylamine was added 0.275 g. (1.45 mmole) of 3,5-dichlorophenylboronic acid and a catalytic amount of tris(dibenzylideneacetone)dipalladium (0), 0.0109 g. (0.012 mmole). The mixture was dissolved in 7 mL of N-methyl-2-pyrrolidinone. Sodium carbonate, 0.105 g. (1.45 mmole) was dissolved in a minimal amount of water and added in one portion to the N-methyl-2-pyrrolidinone reaction solution. The mixture was heated to 80° C. for 10 hours. After cooling to room temperature, the mixture was diluted to 10 mL total volume with methanol and filtered through a silica plug. The title compound was isolated by reverse phase HPLC on a 2 inch Dynamax phenyl column using a solvent gradient from 85:15 methanol:water to 100% methanol, yield 0.320 g. (67%).

Provenance & Evidence