Lithium diisopropylamide → HCID 178482918, compound

Participants

Reaction Steps

Starting with 5-(4-dimethylamino-piperidin-1-yl)-imidazo[4,5-b]pyridin-3-carboxylic acid tert-butyl ester [Example 135, Step 4 (Step 4)] (711 mg, 2.05 mmol) and methyl-2-bromo-isonicotinate (445 mg, 2.05 mmol), the reaction was performed by following General procedure J (LDA metallation) followed by work up method D. Purification by SiO2 chromatography (CH2Cl2/MeOH) gave [5-(4-dimethylamino-piperidin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl]-[2-bromo-pyridin-4-yl]-methanone (350 mg, 40%). 1H NMR (400 MHz, CD3OD) δ 1.43 (m, 2H), 1.93 (m, 2H), 2.26 (s, 6H), 2.47 (m, 1H), 2.87 (m, 2H), 4.53 (m, 2H), 6.95 (d, J=9.54 Hz, 1H), 7.83 (d, J=9.03 Hz, 1H), 8.14 (d, 5.03 Hz, 1H), 8.42 (s, 1H), 8.47 (d, J=5.02 Hz, 1H). MS(ESI) m/z 430 [M+H]+.

Provenance & Evidence