(5-Fluoroquinolin-8-yl)boronic acid → (2S)-2-tert-butoxy-2-(1-(5-fluoroquinolin-8-yl)-3-methylnaphthalen-2-yl)acetic acid

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Reaction Steps

(2S)-2-tert-Butoxy-2-(1-(5-fluoroquinolin-8-yl)-3-methylnaphthalen-2-yl)acetic acid (10) was prepared following the procedure to make (S)-2-tert-butoxy-2-(1-cyclohexenyl-3-methylnaphthalen-2-yl)acetic acid of Example 6 except 5-fluoroquinolin-8-ylboronic acid was used instead of cyclohexenylboronic acid. 1H-NMR: 400 MHz, (CD3OD) δ: 8.81 (d, J=8.2 Hz, 1H), 8.70 (dd, J=3.3 Hz, J=4.7 Hz,1H), 8.09 (t, J=6.2 Hz, 1H), 7.92 (m, 2H), 7.78 (m, 1H), 7.63 (t, J=9.0 Hz, 1H), 7.42 (t, J=7.0 Hz, 1H), 7.18 (t, J=7.8 Hz,1H), 6.84 (d, J=7.6 Hz, 1H), 5.18 (s, 1H), 2.68 (s, 3H), 0.80 (s, 9H). 19F-NMR: 377 MHz, (CD3OD) δ: −77.9, −123.2. LCMS-ESI+ (m/z): [M+H]+ calcd for C26H25FNO3: 418.47. found: 418.1.

Provenance & Evidence