Material was purified employing as a yellow oil (15.four mg, (50 toluene) CDCl3 ) 7.22.14 (m, 4H), six.96.85 (m, 4H), a yellow oil (10.eight mg, 55 1 H NMR (400 MHz,affording 10-methyl-9,10-dihydroacridine 55 as3.89 (s, 2H), 3.38 (s, ten ) 3H); 13 C NMR (101 MHz, CDCl3 ) 143.8, 127.7,yellow 124.5, 120.7, 112.0, 33.4, 33.three ATR-IR benzyl-N-methylaniline 56 as a 127.0, oil (15.4 mg, 14 ). max (neat)/cm-1 2922, 1635, 1595, 1494, 1460, 1367, 1178, 752; GC-MS [m/z ] (14.37 min): 55 1H NMR (400 MHz, CDCl3) 7.22 7.14 (m, 4H), 6.96 six.85 (m, 4H), 3.89 (s, 2H 194 (100, [M-H]), 176 (42), 152 (14), 126 (4), 97 (9), 63 (10). Analytical information are in agreement (s, 3H); the 2-Bromo-6-nitrophenol supplier literature MHz, with these reported in13C NMR (101[74]. CDCl3) 143.8, 127.7, 127.0, 124.5, 120.7, 112.0, 33.four, 33.3 56 1 H NMR (400 max (neat)/cm-1 2922, 1635, 1595, 1494, 1460,(m, 2H), 7.16752; JGC-MS [m/z ] IR MHz, CDCl3 ) 7.32.26 (m, 2H), 7.24.18 1367, 1178, (d, = 7.three Hz, 2H), 7.05.00 (d, J = 7.1 Hz, 1H), six.77 (t, J = 7.four Hz, 1H), six.65 (d, J = 8.1 Hz, 1H), 3.87 (s, 2H), min): 194 (100, [M-H]), 176 (42), 152 (14), 126 (four), 97 (9), 63 (10). Analytical data three.53 (bs, 1H), 2.77 (s, 3H); 13 C NMR (101 MHz, CDCl3 ) 147.three, 139.four, 130.six, 128.eight, 128.six, agreement with those reported in max (neat)/cm-1 128.0, 126.five, 124.7, 117.1, 110.1, 38.0, 30.9; ATR-IRthe literature [74]. : 3431, 2893, 1604, 1512, 1307, 1161, 729. HRMS (ESI): calculated for3) 7.32 N 7.26 (m, ): 198.1277 7.18 (m,198.1277. (d, J = 7 56 1H NMR (400 MHz, CDCl C14 H16 ([MH] 2H), 7.24 identified: 2H), 7.16 NMR information are2H), 7.05 7.00 (d, these reported inside the(t, J = 7.4 Hz, 1H), six.65 (d, J = 8.1 Hz, 1H), 3 in agreement with J = 7.1 Hz, 1H), six.77 literature [75].2H), three.53 (bs, 1H), two.77 (s, 3H); 13C NMR (101 MHz, CDCl3) 147.3, 139.4, 130.6, 128.128.0, 126.5, 124.7, 117.1, 110.1, 38.0, 30.9; ATR-IR max (neat)/cm-1: 3431, 2893, 1604 NMR data are in agreement with those reported inside the literature [75].1307, 1161, 729. HRMS (ESI): calculated for C14H16N ([MH]): 198.1277 found:2H), 7.05 7.00 (d, J = 7.1 Hz, 1H), six.77 (t, J = 7.four Hz, 1H), six.65 (d, J = 8.1 Hz, 1H),2H), 3.53 (bs, 1H), 2.77 (s, 3H); 13C NMR (101 MHz, CDCl3) 147.3, 139.four, 130.six, 128.Molecules 2021, 26,128.0, 126.five, 124.7, 117.1, 110.1, 38.0, 30.9; ATR-IR max (neat)/cm-1: 3431, 2893, 1604 NMR data are in agreement with those reported in the literature [75].three.3.4. Reaction 3.three.4. Reaction of N,2-dimethyl-N-phenylaniline 52 with KOtBu/Et3SiH – neat: of N,2-dimethyl-N-phenylaniline 52 with KOtBu/Et3 SiH–Neat15 of discovered: 198 1307, 1161, 729. HRMS (ESI): calculated for C14H16N ([MH]): 198.1277Substrate 52 (99 mg, 1.0 equiv., (3.0 equiv., KOtBu (three.0 equiv., 1.5 mmol, Substrate 52 (99 mg, 1.0 equiv., 0.five mmol), KOt Bu0.five mmol), 1.5 mmol, 168 mg), and Et3 SiH 168 mg (three.0 equiv., 1.5Et3SiH (3.0 ) were sealed in 240 L) were PF-06454589 LRRK2 sealednitrogen-filled tube inside a nitrogen mmol, 240 equiv., 1.5 mmol, a pressure tube in a inside a stress glovebox. The contents of your pressure tube have been stirred at 130 C for 18 h just before the stress tube glovebox. The contents with the pressure tube had been stirred at 130 for 18 h befo was cooled to area temperature, opened to air and diluted with water (50 mL). The stress extracted into Et2 area 50 mL). The combined organic phases organic goods were tube was cooled also (three emperature, opened to air and diluted with wa had been dried more than Na2 SO4 organic solutions were extracted intomaterial was purified working with mL). The and concentrated in vacuo. The crude Et2O (3 x 50 mL). T.