반응 #992726

반응 방정식

51

N-[17-(5-bromo-6-methoxyisoquinolin-1-yloxy)-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carbonyl](cyclopropyl)sulfonamide

6-methylpyridine-3-boronic acid

sodium carbonate

→

title product 52

수율 21.1%

N-[17-[5-(4-methyl-3-pyridyl)-6-methoxyisoquinolin-1-yloxy]-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carbonyl](cyclopropyl)sulfonamide

수율 21.1%

용매

DMF

반응 조건

후처리

1. 1
   기타the solvent was evaporated
2. 2
   기타The residue was purified by HPLC

실험 절차

A solution of 51 (17.3 mg, 0.025 mmol), 6-methylpyridine-3-boronic acid (5.9 mg, 0.028 mmol), tetrakistriphenylphosphine palladium (8.2 mg, 0.005 mmol) and sodium carbonate (5.8 mg, 0.055 mmol) in DMF (2 mL) were warmed to 90° C. for 20 h. Then, the reaction mixture was cooled down to room temperature and the solvent was evaporated. The residue was purified by HPLC to yield 3.7 mg (21%) of the title product 52 as a white powder. m/z=703 (M+H)+; 1H-NMR (CDCl3): 10.6 (bs, 1H), 8.8 (s, 1H), 8.12 (d, J=9.1 Hz, 1H), 7.97 (d, J=6.3 Hz, 1H), 7.9 (d, J=9.0 Hz, 1H), 7.54 (d, J=6.3 Hz, 1H), 7.3 (d, J=9.0 Hz, 1H), 7.21 (d, J=9.1 Hz, 1H), 6.68 (br s, 1H), 5.87 (br s, 1H), 5.74 (dd, J=17.3 Hz, 8.3 Hz, 1H), 5.16 (t, J=10.4 Hz, 1H), 4.74 (dd, J=9.4 Hz, 7.3 Hz, 1H), 4.11-3.98 (m, 4H), 3.69-3.55 (m, 2H), 3.27-3.10 (m, 1H), 3.02-2.89 (m, 1H), 2.83 (s, 3H), 2.58-2.35 (m, 3H), 2.50 (s, 3H), 2.29-2.13 (m, 1H), 2.11-1.92 (m, 2H), 0.75-1.76 (m, 9H).

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