Nitrogen → {4-[7-(4-Methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-phenyl}-methanol

Participants

Reaction Conditions

Reaction Steps

Charge a 100 mL round bottom flask equipped with: a magnetic stirrer, temperature controlled heating mantle, N2 atmosphere, condenser, with [4-(7-chloro-imidazo[1,2-a]pyridin-3-yl)-phenyl]-methanol (1.11 g, 4.3 mmol), 4-(methylsulfonyl)-phenyl boronic acid (1.27 g, 6.4 mmol), 2-Dicyclohexyl-phosphino-2′,6′-dimethoxy-1,1′-biphenyl (236 mg), Pd(OAc)2 (60 mg), K3PO4 (3.6 g, 16.9 mmol), dioxane: H2O 2:1 (50 mL), EtOH-(3A) (5 mL). Warm the reaction while purging with a N2 needle, then heat to 65° C. for 18 hours. Cool the reaction to room temperature and siphon off the bottom layer (8 mL). Evaporate the reaction under vacuum and dissolve the residue into warm MeOH and filter to remove Pd (0) solids. Rinse the solids with warm MeOH and combine all the MeOHd. (total of 1 L). Evaporate the dissolved crude product under vacuum with 20 g of SiO2 to dryness then chromatograph using SiO2 eluting with a gradient of 0% to 10% of 2 M NH3 in MeOH with the balance CH2Cl2. Dry the product in a vacuum oven at 40° C. for 24 hours to give a yellow solid 1.64 g (100. %) suspect trapped solvent. MS (ES), m/z 379 (M+1).

Provenance & Evidence