Pyridine → 4-allyl-N-(3-chlorophenyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

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Reaction Steps

Preparation of tert-butyl 4-allyl-4-(3-chlorophenylcarbamoyl)piperidine-1-carboxylate. Under an atmosphere of N2, 4-allyl-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (0.158 g, 0.586 mmol), pyridine (0.189 mL, 2.34 mmol), and DMF (3 drops) were dissolved in CH2Cl2 (10 mL) and cooled in an ice bath. To the cooled solution, oxalyl chloride (0.056 mL, 0.645 mmol) was added dropwise. The reaction was stirred for 40 min, after which time 3-chloroaniline (0.061 mL, 0.586 mmol) was added. The reaction was removed from the ice bath and stirred at room temperature overnight. The crude reaction was washed with 1 N aq. HCl and brine, dried over MgSO4, and concentrated under vacuum. The residue was purified by silica gel chromatography (ethyl acetate/hexanes gradient) to give the title compound in 51% yield. MS (ES+) [M+H]+=379.

Provenance & Evidence