Lithium diisopropylamide → HCID 178452222, compound

Participants

Reaction Conditions

Reaction Steps

The mixture of 5-(4-tert-butoxycarbonyl-piperazin-1-yl)-imidazo[4,5-b]pyridine-3-carboxylic acid tert-butyl ester (56 mg, 0.139 mmole), 4-cyano-3-isoquinolin-4-yl-benzoic acid methyl ester (40 mg, 0.139 mmole), and tetrahydrofuran (2 ml) was cooled to −78° C. Lithium diisopropylamide (2N, 0.14 ml, 0.28 mmole) was added slowly. Reaction mixture was stirred at −78° C. for 2 hours and then was quenched with water, extracted with EtOAc. EtOAc layer was concentrated and crude product was purified by using silica gel chromatography, eluting with 20% to 100% EtOAc in heptane to afford 4-[2-(4-cyano-3-isoquinolin-4-yl-benzoyl)-3H-imidazo[4,5-b]pyridine-5-yl]piperazine-1-carboxylic acid tert-butyl ester (18 mg, 23%) as a yellow solid. 1H NMR (400 MHz, CD2Cl2) δ 1.60 (s, 9H), 3.57 (m, 4H), 3.71 (m, 4H), 6.85 (d, J=9.03 Hz, 1H), 7.70 (d, J=7.53 Hz, 1H), 7.78 (m, 2H), 7.95 (d, J=9.03 Hz, 1H), 8.09 (d, J=8.03 Hz, 1H), 8.19 (d, J=8.03 Hz, 1H), 8.62 (s, 1H), 8.84 (s, 1H), 8.89 (d, J=8.53 Hz, 1H), 9.43 (s, 1H), 10.28 (s, 1H). HR-MS m/z 560.2406 (M+1).

Provenance & Evidence