, 114.6, 112.9, 108.5, 99.0, 57.0, 55.5, 26.three, 18.8, four.2. HPLC: 21.73 min., purity at 254 nm 93.7 . HRMS (ESI): m/z calculated for C22H30NO3Si [MH] 384.1989, located 384.1990. 4.1.8. 2(3tertButyldimethylsilyloxy4methoxyphenyl)6,7dimethoxyindole (11)To a option of two,3dimethoxyaniline (two.19 mL, 16.3 mmol) dissolved in N,Ndimethylaniline (20 mL) was added bromoacetophenone 3 (2.93 g, 8.16 mmol). The remedy was heated to reflux and stirred at 150 for 12 h. Upon completion of the reaction, the reaction mixture was cooled to room temperature and extracted with EtOAc (3 50 mL). The combined organic extract was dried over Na2SO4 and concentrated under lowered pressure. Purification by flash chromatography utilizing a prepacked 50 g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 5 A / 95 B (four CV), 5 A / 95 B 40 A / 60 B (ten CV), 40 A / 60 B (two CV); flow rate: 50 mL/min; monitored at 254 and 280 nm] resulted in the preferred six,7dimethoxy2phenylindole 11 (1.43 g, 3.47 mmol, 43 , Rf = 0.40 (80:20 hexanes:EtOAc)) as a tan strong. 1H NMR (CDCl3, 500 MHz): eight.63 (br s, 1H, NH), 7.33 (d, J = 8.five Hz, 1H, ArH), 7.28 (d, J = 2.2 Hz, 1H, ArH), 7.26 (dd, J = 8.five Hz, two.two Hz 1H, ArH), 6.92 (dd, J = eight.4 Hz, 1.4 Hz, 2H, ArH), six.71 (d, J = 2.2 Hz, 1H, ArH), four.15 (s, 3H, OCH3), four.01 (s, 3H, OCH3), three.88 (s, 3H, OCH3), 1.15 (s, 9H, C(CH3)3), 0.31 (s, 6H, Si(CH3)two). 13C NMR (CDCl3, 125 MHz): 150.7, 147.1, 145.four, 137.9, 134.two, 131.two, 126.0, 125.7, 118.4, 118.1, 115.two, 112.three, 108.7, 99.0, 60.9, 57.3, 55.four, 25.eight, 18.five, 4.five. HPLC: 21.28 min., purity at 254 nm 99 . HRMS (ESI): m/z calculated for C23H32NO4Si [MH] 414.2095, found 414.2095. four.1.9. two(3tertButyldimethylsiloxy4methoxyphenyl)3(3, 5dinitrobenzoyl)6methoxyindole (13)To a answer of compound 5 (0.50 g, 1.30 mmol) in odichlorobenzene (20 mL) was added three,5dinitrobenzoylchloride (0.45 g, 1.90 mmol). The reaction mixture was heated to reflux at 160 for 12 h. The odichlorobenzene was removed by basic distillation, and also the resulting dark colored strong was subjected to flash chromatography making use of a prepacked 50 g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 7 A / 93 B (four CV), 7 A / 93 B 60 A / 40 B (11 CV), 60 A / 40 B (2 CV); flow price: 40 mL/min; monitored at 254 and 280 nm] resulting in TBSindole 13 as a pale yellow powder (0.(R)-(1-Methylazetidin-2-yl)methanol In stock 40 g, 0.1256787-10-6 web 69 mmol, 53 , Rf = 0.PMID:23398362 59 (70:30 hexanes:EtOAc)). 1H NMR (CDCl3, 500 MHz): eight.85 (t, J = 2.0 Hz, 1H, ArH), eight.62 (d, J = two.0 Hz, 2H, ArH), 8.60 (br s, 1H, NH) eight.15 (d, J = eight.five Hz, 1H, ArH), 7.00 (dd, J = 8.5 Hz, two.0 Hz, 1H, ArH), six.95 (d, 2.0 Hz, 1H, ArH), 6.87 (dd, J = eight.0 Hz, 2.0 Hz, 1H, ArH), six.61 (d, J = eight.5 Hz, 1H, ArH), 6.56 (d, J = 2.five Hz, 1H, ArH), 3.90 (s, 3H, OCH3), 3.70 (s, 3H, OCH3), 0.89 (s, 9H, C(CH3)three), 0.00 (s, 6H, Si(CH3)two). 13C NMR (CDCl3, 125 MHz): 187.3, 158.1, 152.1, 147.eight, 145.3, 145.1, 143.1, 136.five, 129.1, 123.five, 123.four, 122.7, 122.four, 122.three, 120.1, 112.8, 112.5, 111.eight, 95.0, 55.9, 55.five, 25.six, 18.4, four.eight. HPLC: 20.28 min., purity at 254 nm 93.1 . HRMS (ESI): m/z calculated for C29H32N3O8Si [MH] 578.1953, discovered 578.1950. 4.1.10. two(3tertButyldimethylsiloxy4methoxyphenyl)three(4nitrobenzoyl)6methoxyindole (14)To a resolution of compound five (0.20 g, 0.52 mmol) in odichlorobenzene (10 mL) was added 3nitrobenzoylchloride (0.15 g, 0.78 mmol). The reaction mixture was heated to reflux at 160 for 12 h. The odichlorobenzene was removed by basic distillation, and the resulting dark colored strong was subjected to flash chromatography using a prepacke.