Methyl iodide → HCID 73776851, compound

Participants

Reaction Conditions

Reaction Steps

(180 mg, 574 μmol) 5-(2-Chloro-pyridin-4-ylethynyl)-pyridine-2-carboxylic acid tert-butylamide (Example 1, step 2) was dissolved in DMF (3 ml) and cooled to 0-5° C. Iodomethane (54 μl, 860 μmol, 1.5 equiv.) and NaH (55%) (41 mg, 860 μmol, 1.5 equiv.) were added and the mixture was stirred for 2 hours without cooling bath. The reaction mixture was treated with sat. NaHCO3 solution and extracted twice with EtOAc. The organic layers were extracted with water, dried over sodium sulfate and evaporated to dryness. The crude product was purified by flash chromatography on silica gel (20 g, ethyl acetate/heptane gradient, 0:100 to 100:0). The desired 5-(2-chloro-pyridin-4-ylethynyl)-pyridine-2-carboxylic acid tert-butyl-methyl-amide (78 mg, 42% yield) was obtained as a yellow solid, MS: m/e=328.4/330.4 (M+H+).

Provenance & Evidence