3-Pyridinylboronic acid → 2-Tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-4-(pyridin-3-yl)naphthalen-2-yl)acetic acid

Participants

Reaction Steps

2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-4-(pyridin-3-yl)naphthalen-2-yl)acetic acid (138) was prepared in a manner similar to 2-tert-butoxy-2-(1-(4-chlorophenyl)-3,4-dimethylnaphthalen-2-yl)acetic acid of Example 125, except using pyridin-3-yl-boronic acid in the Suzuki reaction, giving the title compound (mono trifluoroacetic acid salt). 1H-NMR: (400 MHz, DMSO-d6): δ 12.8 (s, broad, 1H), 8.80 (d, J=5.1 Hz, 1H), 8.62 (d, J=12.9 Hz, 1H), 7.97-7.92 (m, 1H), 7.76-7.69 (m, 3H), 7.60-7.54 (m, 1H), 7.47-7.40 (m, 3H), 7.28 (d, J=9.2 Hz, 1H), 7.18 (d, J=9.4 Hz, 1H), 5.15 (s, 1H), 2.25 (s, 3H), 0.96 (s, 9H). 19F-NMR: (377 MHz, DMSO-d6): δ−74.7 (s) LCMS-ESI+ (m/z): [M+H]+ calcd for C28H27ClNO3: 460.2; Found: 460.2.

Provenance & Evidence