Eaction, the reaction mixture was cooled to space temperature and extracted with EtOAc (3 50 mL). The combined organic extract was dried over Na2SO4 and concentrated beneath reduced stress. Purification by flash chromatography applying a prepacked one hundred g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 2 A / 98 B (4 CV), 2 A / 98 B 20 A / 80 B (10 CV), 20 A / 80 B (2 CV); flow price: 40 mL/min; monitored at 254 and 280 nm] resulted inside the preferred 2phenylindole 6 (0.59 g, 1.23 mmol, 44 , Rf = 0.39 (90:10 hexanes:EtOAc)) as a brown solid. 1H NMR (CDCl3, 500 MHz): eight.09 (br s, 1H, NH), 7.37 (d, J = 8.five Hz, 1H, ArH), 7.ten (d, J = 1.5 Hz, 1H, ArH), 7.01 (dd, J = 8.5 Hz, 1.five Hz, 1H, ArH), six.82 (s, 1H, ArH), six.72 (d, J = 8.5 Hz, 1H, ArH), 6.67 (dd, J = eight.five Hz, 1.five Hz, 1H, ArH), six.54 (s, 1H, ArH), three.70 (s, 3H, OCH3), 1.02 (s, 9H, C(CH3)3), 1.01 (s, 9H, C(CH3)3), 0.20 (s, 6H, Si(CH3)two), 0.18 (s, 6H, Si(CH3)2). 13C NMR (CDCl3, 125 MHz): 150.7, 150.six, 145.4, 137.7, 137.three, 126.0, 124.five, 120.6, 118.five, 118.0, 114.six, 112.4, 101.eight, 98.7, 55.four, 25.93, 25.89, 18.six, 18.4, 4.3, 4.five. HPLC: 25.45 min., purity at 254 nm 99 . HRMS (ESI): m/z calculated for C27H42NO3Si2 [MH] 484.2698, discovered 484.2698. 4.1.4. two(3tertButyldimethylsilyloxy4methoxyphenyl)four,five,6trimethoxyindole (7)To a option of 3,four,5trimethoxyaniline (0.336 g, 1.84 mmol) in N,Ndimethylaniline (20 mL) at 170 was added compound three (0.20 g, 0.56 mmol) dropwise in EtOAc (five mL). The reaction mixture was stirred at 170 for 12 h. Upon completion on the reaction, the reaction mixture was cooled to space temperature and extracted with EtOAc (three 50 mL). The combined organic extract was dried more than Na2SO4 and concentrated below decreased pressure. Purification by flash chromatography utilizing a prepacked 50 g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 7 A / 93 B (4 CV), 7 A / 93 B 60 A / 40 B (10 CV), 60 A / 40 B (2 CV); flow rate: 40 mL/min; monitored at 254 and 280 nm] resulted inside the desired 2phenylindole 7 (0.14 g, 0.32 mmol, 58 , Rf = 0.31 (70:30 hexanes:EtOAc)) as colorless crystals.Buy5-Chloro-1H-pyrazolo[4,3-d]pyrimidine 1H NMR (CDCl3, 500 MHz): 8.06 (br s, 1H, NH), 7.15 (dd, J = eight.five Hz, 2.0 Hz, 1H, ArH), 7.ten (d, J = two.0 Hz, 1H, ArH), 6.90 (d, J = eight.5 Hz, 1H, ArH), 6.70 (dd, J = two.0 Hz, 1.0 Hz, 1H, ArH), six.66 (d, J = 0.five Hz, 1H, ArH), four.13 (s, 3H, OCH3), 3.90 (s, 3H, OCH3), 3.6-Chlorofuro[3,4-c]pyridin-1(3H)-one Order 88 (s, 3H, OCH3), 3.PMID:25804060 84 (s, 3H, OCH3), 1.03 (s, 9H, C(CH3)3), 0.19 (s, 6H, Si(CH3)two). 13C NMR (CDCl3, 125 MHz): 151.0, 150.six, 145.six, 145.five, 136.four, 135.8, 133.9, 125.8, 118.3, 117.9, 116.6, 112.5,NIHPA Author Manuscript NIHPA Author Manuscript NIHPA Author ManuscriptBioorg Med Chem. Author manuscript; obtainable in PMC 2014 November 01.MacDonough et al.Page96.three, 89.8, 61.6, 60.9, 56.two, 55.two, 25.9, 18.5, four.six. HPLC: 20.17 min., purity at 254 nm 94.2 . HRMS (ESI): m/z calculated for C24H34NO5Si [MH] 444.2201, discovered 444.2200. 4.1.5. two(4Methoxyphenyl)six,7dimethoxyindole (8)To a resolution of 2,3dimethoxyaniline (0.92 mL, six.85 mmol) dissolved in N,Ndimethylaniline (ten mL) was added 4methoxybromoacetophenone four (0.79 g, three.43 mmol). The option was heated to reflux and stirred at 150 for 12 h. Upon completion on the reaction, the reaction mixture was cooled to room temperature and extracted with EtOAc (three 50 mL). The combined organic extract was dried more than Na2SO4 and concentrated beneath reduced pressure. Purification by flash chromatography making use of a prepacked one hundred g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 5 A / 95 B (4 CV), 5 A / 95.