((1E)-prop-1-en-1-yl)boronic acid → (E)-N,N-Dibutyl-4-chloro-1-(4-(1-ethyl-5-(prop-1-enyl)indolin-6-ylsulfonylcarbamoyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-5-methyl-1H-pyrazole-3-carboxamide

Participants

Reaction Steps

Following a procedure analogous to that for the synthesis of Example 87, 1-(4-(5-bromo-1-ethylindolin-6-ylsulfonylcarbamoyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-N,N-dibutyl-4-chloro-5-methyl-1H-pyrazole-3-carboxamide (Example 71, 35 mg, 0.042 mmol) and (E)-prop-1-enylboronic acid (14 mg, 0.17 mmol) were converted to the title compound (8 mg, 22%) as a white solid. 1H NMR (CD3OD, 2:1 mixture of amide rotamers) δ 8.03-7.99 (m, 1H), 7.88-7.87 (m, 1H), 7.72-7.67 (m, 1H), 7.31-7.12 (m, 6.5H), 6.94-6.93 (m, 0.5H), 6.05-5.90 (m, 1H), 4.75-4.40 (m, 2H), 3.95-3.55 (m, 1H), 3.47 (t, J=8.4 Hz, 2H), 3.27-3.15 (m, 2H), 3.26 (q, J=7.0 Hz, 2H), 3.01 (t, J=7.9 Hz, 2H), 2.80-2.60 (m, 2H), 2.34 (s, 2H), 2.30 (s, 1H), 2.09-2.07 (m, 1H), 1.85-1.83 (m, 2H), 1.55-0.90 (m, 14H), 0.95-0.87 (m, 3H), 0.77 (t, J=7.3 Hz, 2H), 0.70 (t, J=7.4 Hz, 1H); MS(ESI+) m/z 799.4 (M+H)+.

Provenance & Evidence