Dichloromethane → HCID 86686735, compound

Participants

Reaction Conditions

Reaction Steps

To 5-chloro-3-iodo-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (example 19, step 1, 2.50 g, 4.52 mmol) was added 6-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (2.05 g, 4.52 mmol), K2CO3 (1.87 g, 13.56 mmol), PdCl2(dppf).CH2Cl2 (0.37 g, 0.45 mmol), dioxane (36 mL) and H2O (9 mL). The resulting mixture was heated at 40° C. for 16 hours, at which time LC/MS analysis confirmed full consumption of starting material. On cooling, H2O (20 mL) and CH2Cl2 (50 mL) were used to transfer the reaction mixture to a separatory funnel. Brine (30 mL) was added and organics were extracted with CH2Cl2 (4×50 mL), dried (Na2SO4) and concentrated in vacuo to give a black oil. Gradient column chromatography on silica eluting with 10% to 30% EtOAc/hexanes gave 5-chloro-3-(6-fluoroquinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine as a light yellow solid (1.89 g, 3.30 mmol, 73%). LC/MS: 3.22 mins, m/z=574.2 (MH+).

Provenance & Evidence