Methyl 4-bromopicolinate → 2-(2,3-Dimethylphenoxy)ethyl 5-(3-((3-tert-butoxy-3-oxopropylcarbamoyloxy)methyl)phenyl)-3,4-dihydroquinoline-1 (2H)-carboxylate

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Reaction Steps

The title compound was prepared using a procedure analogous to methyl 4-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)picolinate except that 4-(2,3-dimethylphenoxy)-1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-one was replaced by tert-butyl 3-((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyloxy)carbonylamino)propanoate, and methyl 4-bromopicolinate was replaced by 2-(2,3-dimethylphenoxy)ethyl 5-bromo-3,4-dihydroquinoline-1(2H)-carboxylate. LCMS, [M-tBu+2H]+=547.2. 1H NMR (400 MHz, CDCl3) δ 7.64 (d, J=8.1 Hz, 1H), 7.46-7.35 (m, 2H), 7.34-7.27 (m, 1H), 7.27-7.20 (m, 1H), 7.16 (t, J=7.9 Hz, 1H), 7.03 (t, J=7.9 Hz, 1H), 6.97 (d, J=7.5 Hz, 1H), 6.79 (d, J=7.7 Hz, 1H), 6.70 (d, J=8.1 Hz, 1H), 5.12 (s, 2H), 4.60-4.52 (m, 2H), 4.24-4.19 (m, 2H), 3.73 (t, J=6.4 Hz, 2H), 3.41 (dd, J=12.0, 6.0 Hz, 2H), 2.57 (t, J=6.3 Hz, 2H), 2.44 (t, J=5.9 Hz, 2H), 2.26 (s, 3H), 2.17 (s, 3H), 1.86-1.75 (m, 2H), 1.42 (s, 9H).

Provenance & Evidence