144.5, 141.5, 136.six, 131.three (q, JCF = 33 Hz), 129.7 (m), 124.47 (q, Jcf = 7 Hz), 124.46, 124.0, 123.1 (q, JCf = 275 Hz), 122.9, 122.7, 122.five, 122.two, 112.4, 112.1, 94.9, 55.8, 55.5, 25.6, 18.4, four.eight. 19F NMR (CDCl3, 470 MHz): 62.eight (s, 6F, CF3). HPLC: 22.22 min., purity at 254 nm 96.3 . HRMS (ESI): m/z calculated for C31H32F6NO4Si [M H] 624.1999, found 624.1997. 4.1.15. (two(3tertButyldimethylsilyloxy4methoxyphenyl)three(3trifluoromethoxybenzoyl)6methoxyindole (19)To a solution of compound five (1.14 g, 2.97 mmol) in odichlorobenzene (15 mL) was added 3trifluoromethoxybenzoyl chloride (0.70 mL, four.45 mmol). The reaction mixture was heated to reflux at 170 for 12 h. The odichlorobenzene was removed by uncomplicated distillation, as well as the resulting dark green colored strong was subjected to flash chromatography employing 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 (10 CV), 60 A / 40 B (two CV); flow price: 40 mL/min; monitored at 254 and 280 nm] resulting in TBSindole 19 as a yellow powder (1.21 g, 2.11 mmol, 71 , Rf = 0.43 (70:30 hexanes:EtOAc)). 1H NMR (CDCl3, 500 MHz): eight.31 (br s, 1H, NH), 7.96 (d, J = eight.four Hz, 1H, ArH), 7.52 (dt, J = 7.5 Hz, 1.three Hz, 1H, ArH) 7.48 (s, 1H, ArH), 7.17 (t, J = 7.eight Hz, 1H, ArH), 7.13 (d, J = 8.2 Hz, 1H, ArH), six.93 (m, 2H, ArH), 6.81 (m, 2H, ArH), 6.62 (d, J = 9.0 Hz, 1H, ArH), three.88 (s, 3H, OCH3), three.73 (s, 3H, OCH3), 0.97 (s, 9H, C(CH3)three), 0.08 (s, 6H, Si(CH3)two). 13C NMR (CDCl3, 125 MHz): 191.eight, 157.four, 151.6, 148.8, 144.9, 144.1, 142.1, 136.six, 129.two, 128.0, 124.three, 123.six, 123.five, 122.9, 122.2, 122.0, 121.four, 120.4 (q, JCF = 256 Hz), 112.6, 112.0, 111.6, 94.8, 55.7, 55.three, 25.7, 18.4, 4.7. 19F NMR (CDCl3,NIHPA Author Manuscript NIHPA Author Manuscript NIHPA Author ManuscriptBioorg Med Chem. Author manuscript; accessible in PMC 2014 November 01.MacDonough et al.Page470 MHz): 57.8 (s, 3F, OCF3). HPLC: 21.53 min., purity at 254 nm 99 . HRMS (ESI): m/z calculated for C30H33F3NO5Si [MH] 572.2075, located 572.2071.NIHPA Author Manuscript NIHPA Author Manuscript NIHPA Author Manuscript4.1.16. (2(3tertButyldimethylsilyloxy4methoxyphenyl)three(4trifluoromethoxybenzoyl)6methoxyindole (20)To a answer of compound five (1.4-Chloro-2-butenoic acid custom synthesis 14 g, two.97 mmol) in odichlorobenzene (15 mL) was added 4trifluoromethoxybenzoyl chloride (0.70 mL, four.45 mmol). The reaction mixture was heated to reflux at 170 for 12 h.Formula of 2369772-11-0 The odichlorobenzene was removed by basic distillation, and the resulting dark green colored solid was subjected to 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 (ten CV), 60 A / 40 B (1.1 CV); flow rate: 40 mL/min; monitored at 254 and 280 nm] resulting in TBSindole 20 as a yellow powder (0.PMID:24428212 92 g, 1.61 mmol, 54 , Rf = 0.43 (70:30 hexanes:EtOAc)). 1H NMR (CDCl3, 500 MHz): 8.29 (br s, 1H, NH), eight.00 (d, J = 8.six Hz, 1H, ArH), 7.64 (d, J = eight.7 Hz, 2H, ArH) 6.97 (d, J = 8.0 Hz, 2H, ArH), six.93 (m, 2H, ArH), six.83 (d, J = 2.two Hz, 1H, ArH), 6.73 (dd, J = 8.three Hz, 2.2 Hz, 1H, ArH), 6.58 (d, J = 8.4 Hz, 1H, ArH), three.88 (s, 3H, OCH3), three.73 (s, 3H, OCH3), 0.98 (s, 9H, C(CH3)3), 0.10 (s, 6H, Si(CH3)2). 13C NMR (CDCl3, 125 MHz): 191.9, 157.3, 151.six, 151.0, 144.8, 144.1, 138.four, 136.six, 131.3, 124.2, 123.8, 122.eight, 122.2, 121.4, 120.3 (q, JCF = 256 Hz), 119.7, 112.six, 111.9, 111.3, 94.eight, 55.six, 55.1, 25.six, 18.four, four.eight. 19F NMR (CDCl3, 470 MHz): 57.7 (s, 3F, OCF3). HPLC: 21.61 min., purity at 254 nm 99 . HRMS (ESI).