Potassium Carbonate → HCID 86727363, compound

Participants

Reaction Steps

A degassed mixture of 4-(7-bromo-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl)-piperidine-1-carboxylic acid tert-butyl ester (Preparation #1, Step D, 1.70 g, 5.74 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (3.55 g, 11.48 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)dichloride dichloromethane complex (0.494 g, 0.675 mmol) and K2CO3 (1.58 g, 11.48 mmol) in dioxane (10 mL) and water (2 mL) was heated to reflux for 6 h. The reaction mixture was cooled to ambient temperature and filtered through a pad of Celite®. The filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 40% EtOAc in petroleum ether) to give 4-(4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (2.0 g, 87%) as a pale white solid. LC/MS (Table 1, Method 3) Rt=1.398 min.; MS m/z: 399 [M+H]+.

Provenance & Evidence