Potassium Carbonate → 1,1-Dimethylethyl 4-[(6-amino-3-pyridinyl)methyl]-1-piperidinecarboxylate

Participants

Reaction Conditions

Reaction Steps

Stir for 5 min 4-methylene-piperidine-1-carboxylic acid tert-butyl ester (5.10 g) under nitrogen and add a 0.5 M THF solution of 9-borabicyclo[3.3.1]nonane (77.49 mL). Stir at 75° C. under nitrogen for 1 h. Cool and add 2-amino-5-bromopyridine (3.8 g), potassium carbonate (3.87 g), and 1,1′-biss(diphenylphosphino)ferrocene)palladium(II) chloride (538.10 mg) and a degassed mixture of DMF (47.83 mL) and water (4.78 mL). Stir at 60° C. during 4 h, then at RT over the weekend. Add water and EA. Separate and extract aqueous layer with EA. Combine the organic layers and dry over sodium sulfate and remove the solvent under vacuum. Purify by silica gel column chromatography, eluting with DCM/methanol (1%)/ammonia (0.1%) to DCM/methanol (3%)/ammonia (0.3%). Triturate the residue with EA to afford 1.85 g of the title compound. MS (ES+): m/z=292 (M+H)+.

Provenance & Evidence