Cesium carbonate → [2-(5-Chloro-2-fluoro-phenyl)-quinolin-4-yl]-(3-methoxy-pyridin-4-yl)-amine

Participants

Reaction Steps

250 mg 4-Bromo-2-(5-chloro-2-fluoro-phenyl)-quinoline (cf. Example 5; M 336.59) and 94 mg of 3-methoxy-4-amino pyridine (Tyger Scientific) in 25 ml dioxane were treated under argon with 14 mg Pd2(dba)3 (Aldrich) and 22 mg Xanthphos (ABCR) under basic conditions adjusted with 485 mg Cs2CO3 at 85° C. internal temperature over night. Work-up was conducted by RP HPLC on a Gemini column Axia RP18-100×30 mm/10 μm-110 A. Elution was performed with a 30 min gradient of 1-99% buffer B (=0.3% TFA in CH3CN) in buffer A (=0.3% TFA in water) at 30 ml/min and monitoring at 215 nm. Pooled material after drying yielded 228 mg product of correct mass M+H+ 380 and Rt˜1.74 min in LC-MS system 2.

Provenance & Evidence