1,4-Dioxane → HCID 66599736, compound

Participants

Reaction Conditions

Reaction Steps

To 2-bromonicotinic acid methyl ester (30 g, 111 mmol), isoquinoline-4-boronic acid (20 g, 92.6 mmol), 1,4-dioxane (770 mL) and 3M aqueous K3PO4 (35 mL, 105 mmol) were stirred together. The vessel was evacuated and flushed with nitrogen several times to remove oxygen. PdCl2(PPh3)2 (1.62 g, 1.85 mmol) was added and the vessel and the stirred mixture was heated at 70° C. overnight. The mixture was then cooled, concentrated in vacuo to 50% of original volume and filtered. The filtrate was concentrated in vacuo and the resulting residue stirred in butylmethylether (220 mL). The mixture was then filtered to remove solid. The filtrate was cooled in an ice bath and stirred for 1 hour after which time the product precipitated as a white solid. The product was collected and dried to give isoquinolin-4-yl-isonicotinic acid methyl ester (4.97 g, 16%) (combined from two crops) [M+H]+:264.7.

Provenance & Evidence