(1-(tert-Butoxycarbonyl)-2,2,4-trimethyl-1,2-dihydroquinolin-6-yl)boronic acid → 6-(3-Cyano-2-methylphenyl)-1,2-dihydro-2,2,4-trimethylquinoline

Participants

Reaction Steps

This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (56.5 mg, 0.18 mmol) and 3-bromo-2-methylbenzonitrile (34.8 mg, 0.18 mmol). The crude material was purified by flash column chromatography (50 ml silica, hexane to 20% acetone/hexane) followed by a second flash column chromatography (75 mL silica, hexane to 20% acetone/hexane to afford 10.5 mg (20%) of Compound 278. Data for Compound 278: 1H NMR (400 MHz, acetone-d6) 7.59 (dd, J=7.7, 0.9, 1 H), 7.48 (dd, J=7.8, 0.8, 1 H), 7.36 (t, J=15.3, 7.7, 1 H), 6.99 (d, J=1.8, 1 H), 6.91 (dd, J=8.1, 1.9, 1 H), 6.58 (d, J=8.1, 1 H), 5.37 (s, 1 H), 5.30 (s, 1 H), 2.48 (s, 3 H), 1.97 (s, 3 H), 1.30 (s, 6 H).

Provenance & Evidence