Reaction Steps
Prepared using General Procedure 3. To a solution of 5-(4-(1-((tert-butyldimethylsilyl)oxy)-2,3-dihydro-1H-inden-4-yl)thiophen-2-yl)-2-isopropoxybenzonitrile (17 mg, 0.03 mmol) in THF (1 mL) was added 1M solution of TBAF in tetrahydrofuran (0.3 mL, 0.3 mmol) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated and purified by preparative HPLC to yield 8 mg (46%) of 5-(4-(1-hydroxy-2,3-dihydro-1H-inden-4-yl)thiophen-2-yl)-2-isopropoxybenzonitrile 226 as white solid. LCMS-ESI (m/z) calculated for C23H21NO2S: 375.1; found 398.1 [M+Na]+. tR=3.84 min; 1H NMR (400 MHz, CDCl3) δ 7.78 (d, J=2.3 Hz, 1H), 7.72 (dd, J=8.8, 2.4 Hz, 1H), 7.43-7.36 (m, 2H), 7.35-7.28 (m, 1H), 7.26 (d, J=1.4 Hz, 1H), 7.24 (s, 1H), 7.06-6.89 (m, 1H), 5.29 (t, J=6.1 Hz, 1H), 4.77-4.49 (m, 1H), 3.20 (ddd, J=16.0, 8.4, 4.7 Hz, 1H), 3.01-2.86 (m, 1H), 2.50 (dddd, J=13.0, 8.1, 6.8, 4.7 Hz, 1H), 2.11-1.88 (m, 1H), 1.58 (s, 1H), 1.41 (d, J=6.1 Hz, 6H); 13 NMR (101 MHz, CDCl3) δ 159.51, 146.35, 142.55, 142.00, 140.88, 133.16, 131.79, 131.24, 128.14, 127.69, 127.56, 124.16, 123.54, 122.06, 116.54, 114.39, 103.84, 76.68, 72.45, 36.28, 30.50, 22.08.
