144.five, 141.5, 136.6, 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.eight, 55.five, 25.6, 18.4, 4.eight. 19F NMR (CDCl3, 470 MHz): 62.8 (s, 6F, CF3). HPLC: 22.22 min., purity at 254 nm 96.three . HRMS (ESI): m/z calculated for C31H32F6NO4Si [M H] 624.1999, found 624.1997. four.1.15. (2(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, 4.45 mmol). The reaction mixture was heated to reflux at 170 for 12 h. The odichlorobenzene was removed by straightforward distillation, plus the resulting dark green colored solid was subjected to flash chromatography applying 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 (ten 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, two.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 = 8.4 Hz, 1H, ArH), 7.52 (dt, J = 7.5 Hz, 1.three Hz, 1H, ArH) 7.48 (s, 1H, ArH), 7.17 (t, J = 7.8 Hz, 1H, ArH), 7.13 (d, J = eight.2 Hz, 1H, ArH), 6.93 (m, 2H, ArH), 6.81 (m, 2H, ArH), six.62 (d, J = 9.0 Hz, 1H, ArH), three.88 (s, 3H, OCH3), 3.73 (s, 3H, OCH3), 0.97 (s, 9H, C(CH3)3), 0.08 (s, 6H, Si(CH3)two). 13C NMR (CDCl3, 125 MHz): 191.eight, 157.4, 151.six, 148.8, 144.9, 144.1, 142.1, 136.6, 129.two, 128.0, 124.three, 123.6, 123.five, 122.9, 122.two, 122.0, 121.four, 120.four (q, JCF = 256 Hz), 112.six, 112.0, 111.six, 94.8, 55.7, 55.3, 25.7, 18.four, 4.7. 19F NMR (CDCl3,NIHPA Author Manuscript NIHPA Author Manuscript NIHPA Author ManuscriptBioorg Med Chem. Author manuscript; readily available in PMC 2014 November 01.MacDonough et al.Page470 MHz): 57.eight (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 5 (1.661487-17-8 Chemscene 14 g, 2.Buy(1-Methylcyclopentyl)methanol 97 mmol) in odichlorobenzene (15 mL) was added 4trifluoromethoxybenzoyl chloride (0.PMID:33653245 70 mL, 4.45 mmol). The reaction mixture was heated to reflux at 170 for 12 h. The odichlorobenzene was removed by basic distillation, along with the resulting dark green colored strong was subjected to flash chromatography applying 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 (ten CV), 60 A / 40 B (1.1 CV); flow price: 40 mL/min; monitored at 254 and 280 nm] resulting in TBSindole 20 as a yellow powder (0.92 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 = 8.7 Hz, 2H, ArH) 6.97 (d, J = 8.0 Hz, 2H, ArH), 6.93 (m, 2H, ArH), six.83 (d, J = two.2 Hz, 1H, ArH), six.73 (dd, J = 8.3 Hz, two.two Hz, 1H, ArH), 6.58 (d, J = 8.4 Hz, 1H, ArH), three.88 (s, 3H, OCH3), 3.73 (s, 3H, OCH3), 0.98 (s, 9H, C(CH3)3), 0.ten (s, 6H, Si(CH3)2). 13C NMR (CDCl3, 125 MHz): 191.9, 157.three, 151.six, 151.0, 144.eight, 144.1, 138.four, 136.six, 131.three, 124.2, 123.eight, 122.eight, 122.two, 121.4, 120.three (q, JCF = 256 Hz), 119.7, 112.six, 111.9, 111.3, 94.eight, 55.6, 55.1, 25.6, 18.4, 4.8. 19F NMR (CDCl3, 470 MHz): 57.7 (s, 3F, OCF3). HPLC: 21.61 min., purity at 254 nm 99 . HRMS (ESI).