Sodium Carbonate → HCID 86669235, compound

Participants

Reaction Steps

To a solution of [(cis)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]formamide (for a preparation see Intermediate 43) (82 g, 0.263 mol) in DME (2 L) are added (4-formylphenyl)boronic acid (51.4 g, 0.34 mol) at room temperature. A 2N solution of Na2CO3 (527 mL, 1.05 mol) and tetrakis(triphenylphosphine)palladium(0) (8.2 g, 10% w/w) are added and the mixture is heated to reflux under a nitrogen atmosphere. After 2 hours, the reaction is complete and the mixture is concentrated under reduced pressure. The residue is taken up in water (1 L) and the darkened mixture is diluted with EtOAC (1 L) and transferred to a separatory funnel. A dark precipitate has formed and is isolated by filtration after separation of the organic phase. The organic layer is dried over Na2SO4 and delivers the title compound (37.5 g) as a yellow solid after concentration under reduced pressure and precipitation of the organic residue in a DCM/hexane mixture. The dark solid is taken up in a DCM/MeOH mixture and purified by flash chromatography on silica gel eluting with a 80/2 ratio of DCM/MeOH to afford the title compound (45 g) as a yellow brown solid. Mp: 85.6° C.

Provenance & Evidence