Sodium Carbonate → 4-Ethynyl-2-(2-nitro-5-(piperidin-1-yl)phenyl)pyridine

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Reaction Conditions

Reaction Steps

A degassed mixture of 2-chloro-4-((trimethylsilyl)ethynyl)pyridine 24a, boronic ester 1.1e, 4.9 mL of 2 M aqueous Na2CO3, and 12 mL of DME was treated with 45 mg of XPHOS and 11 mg of Pd(OAc)2. The mixture was stirred at 75° C. for 1.5 h. The solvent was evaporated at reduced pressure and the residue was dissolved in 100 mL of dichloromethane. The solution was washed with water and dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel chromatography eluting with a 0-20% gradient of EtOAc in CH2Cl2 to give 275 mg of product. MS (ESI, m/z) 308.1 [M+H]+.

Provenance & Evidence