: m/z calculated for C30H33F3NO5Si [MH] 572.2075, located 572.2075. four.1.17. 2(3tertButyldimethylsiloxy4methoxyphenyl)three(three,4,5trimethoxybenzoyl)6tertbutyldimethylsiloxyindole (21)To a solution of compound 6 (0.19 g, 0.39 mmol) in odichlorobenzene (20 mL) was added 3,4,5trimethoxybenzoyl chloride (0.13 g, 0.58 mmol). The reaction mixture was heated to reflux at 160 for 12 h. The odichlorobenzene was removed by easy distillation, as well as the resulting dark colored solid was subjected to flash chromatography working with 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 (2 CV); flow rate: 40 mL/min; monitored at 254 and 280 nm] resulting in diTBSindole 21 as a pale yellow powder (0.04 g, 0.59 mmol, 20 , Rf = 0.33 (70:30 hexanes:EtOAc)). 1H NMR (CDCl3, 500 MHz): eight.31 (br s, 1H, NH), 7.90 (d, J = 8.5 Hz, 1H, ArH), six.99 (s, 2H, ArH) six.94 (dd, J = eight.five Hz, 2.0 Hz, 1H, ArH), six.89 (d, J = 2.0 Hz, 1H, ArH), six.82 (dd, J = eight.five Hz, two.0 Hz, 1H, ArH), six.76 (d, J = 2.five Hz, 1H, ArH), six.70 (d, J = 8.0 Hz, 1H, ArH), 3.79 (s, 3H, OCH3), 3.75 (s, 3H, OCH3), 3.69 (s, 6H, OCH3), 1.01 (s, 9H, C(CH3)3), 0.94 (s, 9H, C(CH3)three), 0.22 (s, 6H, Si(CH3)2), 0.04 (s, 6H, Si(CH3)two). 13C NMR (CDCl3, 125 MHz): 191.8, 153.0, 152.six, 151.7, 145.two, 142.3, 141.3, 136.five, 134.six, 125.2, 123.9, 122.3, 121.9, 116.7, 112.9, 111.8, 107.4, 105.1, 101.6, 60.9, 56.1, 55.five, 25.9, 25.8, 18.46, 18.45, four.two, 4.8. HPLC: 23.31 min., purity at 254 nm 90.6 . HRMS (ESI): m/z calculated for C37H52NO7Si2 [MH] 678.3277, identified 678.3279. four.1.18. 2(3tertButyldimethylsiloxy4methoxyphenyl)three(three,4,5trimethoxybenzoyl)four,5,6trimethoxyindole (22)To a resolution of compound 7 (0.05 g, 0.11 mmol) in odichlorobenzene (ten mL) was added three,four,5trimethoxybenzoyl chloride (0.04 g, 0.17 mmol). The reaction mixture was heated to reflux at 160 for 12 h. The odichlorobenzene was removed by easy distillation, and also the resulting dark green colored strong was subjected to flash chromatography working with a prepacked 25 g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 12 A / 88 B (4 CV), 12 A / 88 B one hundred A / 0 B (ten CV), 100 A / 0 B (two CV); flow rate: 25 mL/min; monitored at 254 and 280 nm] resulting in TBSindole 22 as a pale yellow powder (0.03 g, 0.05 mmol, 46 , Rf = 0.50 (50:50 hexanes:EtOAc)). 1H NMR (CDCl3, 500 MHz): 8.25 (br s, 1H, NH), 7.19 (s, 2H,Bioorg Med Chem. Author manuscript; accessible in PMC 2014 November 01.MacDonough et al.PageArH), six.99 (dd, J = 8.five Hz, two.five Hz, 1H, ArH), 6.88 (d, J = two.five Hz, 1H, ArH), six.75 (d, J = 8.0 Hz, 1H, ArH), 6.69 (s, 1H, ArH), three.90 (s, 3H, OCH3), three.85 (s, 3H, OCH3), three.82 (s, 3H, OCH3), three.76 (s, 3H, OCH3), 3.Mc-Val-Cit-PABC-PNP Order 74 (s, 6H, OCH3), three.1417789-17-3 Data Sheet 72 (s, 3H, OCH3), 0.93 (s, 9H, C(CH3)3), 0.PMID:33629228 04 (s, 6H, Si(CH3)two). 13C NMR (CDCl3, 125 MHz): 193.four, 152.9, 152.1, 151.4, 146.four, 145.three, 142.2, 137.8, 136.six, 134.2, 132.four, 124.7, 121.1, 120.five, 116.7, 114.4, 112.3, 107.6, 89.eight, 61.four, 61.0, 60.8, 56.four, 56.3, 55.six, 25.8, 18.five, 4.7. HPLC: 18.60 min., purity at 254 nm 90.7 . HRMS (ESI): m/z calculated for C34H44NO9Si [MH] 638.2780, located 638.2780. 4.1.19. two(4Methoxyphenyl)three(3,4,5trimethoxybenzoyl)6methoxy7tertbutyldimethylsilyloxyindole (23)To a option of compound 10 (0.05 g, 0.13 mmol) in odichlorobenzene (10 mL) was added 3,four,5trimethoxybenzoyl chloride (0.05 g, 0.20 mmol). The reaction mixture was heated to reflux at 160 for 12 h. The odichlorobenzene was removed by uncomplicated distillation, along with the resulting dark green colored.
