Sodium Carbonate → 5-[2-(2-Chloro-pyridin-4-yl)-quinazolin-4-yl]-(1S,4S)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 5-(2-chloro-quinazolin-4-yl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (0.145 g, 0.4 mmol) in DME (2 mL) under nitrogen were added palladium acetate (0.0045 g, 0.02 mmol), tri-o-tolylphosphine (0.015 g, 0.048 mmol), and 2-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine (0.19 g, 0.8 mmol), followed by 2M Na2CO3 (0.6 mL, 1.2 mmol). The resulting mixture was heated at 80° C. for 20 h. The reaction was diluted with methylene chloride and washed with saturated sodium bicarbonate and brine and dried (MgSO4). Flash chromatography of the crude product mixture with 25:10:65, 35:10:55, and 50:10:40 EtOAc-CH2Cl2-Hexane gave the title compound. MS (ES+): 438.2 [M+H]+.

Provenance & Evidence