Nanocrystalline Magnesium Oxide-Stabilized Palladium(0): An Efficient and Reusable Catalyst for the Synthesis of N-(2- pyridyl)indoles

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1 Electronic Supplementary Material (ESI) for ew Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre ational de la Recherche Scientifique 2015 Supplementary Material (ESI) for ew Journal of Chemistry This journal is (c) The Royal Society of Chemistry anocrystalline Magnesium Oxide-Stabilized Palladium(0): An Efficient and Reusable Catalyst for the Synthesis of -(2- pyridyl)indoles Police Vishnuvardhan Reddy, Manne Annapurna, Pottabathula Srinivas, Pravin R Likhar and Mannepalli Lakshmi Kantam* I & PC Division, CSIR- Indian Institute of Chemical Technology, Hyderabad , India. Fax : ; Table of Contents 1. General information 2 2. Preparation and characterization of the catalyst 2 3. General producer for the synthesis of -(2-pyridyl)indoles 3 4. Spectroscopic data 4 5. References H 1 and C 13 spectra copies of products 12 1

2 General Information: AP-MgO (commercial name: anoactive Magnesium Oxide Plus, Specific surface area = 590 m 2 /g) was purchased from anoscalematerials, Inc. (Manhattan, USA). All chemicals were purchased commercially and were used as received. All solvents used for experiments were dried using standard procedures and distilled prior to use. The particle size and morphology of the samples were studied using Philips TECAI F12 FEI Transmission Electron Microscope (TEM). All known compounds were characterized and compared with the literature reports. The 1 H MR and 13 C MR spectra were recorded on a Bruker-Avance (300 MHz) and Avance (500MHz) spectrophotometer using CDCl 3 solvents, and TMS as the internal standard. ESI-MS spectra were determined on a LCQ iontrap mass spectrometer (Thermo Fisher, San Jose, CA, USA), equipped with an ESI source. HRMS spectra were determined on QSTAR XL (Applied Biosystems/MDSSciex, Foster city, USA). The data acquired in positive ionization mode. X-ray diffraction data were collected from single crystal on a D8 Bruker diffractometer with APEX2 area detector using graphite mono chromated Mo-K radiation ( = Å) from a 1μS micro source. Geometric and intensity data were collected using SMART software. The data were processed using SAIT and corrections for absorption were applied using SADABS. The structure was solved by direct methods and refined with full-matrix least-squares methods on F 2 using the SHELX-TL package. The structure contains heavily disordered solvent. Therefore, the data set was treated with SQUEEZE as implemented in WinGX PLATO (WinGX version 1.64). Preparation of the catalyst: Preparation of anocrystalline MgO stabilized Palladium Catalyst AP-Mg-PdCl 4 : AP-MgO was calcined in air at 450 C for four hours (1.0g) and treated with a 2 PdCl 4 (0.294g, 1 mmol) dissolved in 100 ml decarbonated water with vigorous stirring for 12 h at room temperature under nitrogen atmosphere to afford the brown colored AP-Mg- PdCl 4. Then the catalyst was filtered and washed with deionized water and acetone and dried under vacuum. 2

3 AP-Mg-Pd(0): AP-Mg-PdCl 4 (1.0g) was reduced with sodium borohydride (1.5g, 39.6 mmol) in 20 ml of dry ethanol with vigorous stirring for 3 h at under a nitrogen atmosphere at room temperature. Then the reduced catalyst was filtered through a G-3 sintered glass funnel and washed with deionized water and acetone and dried under vacuum to get the black-colored, air stable AP-Mg-Pd(0). Catalyst Characterization: SEM-EDX analysis: The scanning electron microscopy-energy dispersive X-ray analysis of fresh and used AP-Mg- Pd(0) catalysts showed 0.88 and 0.89 mmolg -1 of Pd respectively. General producer for the synthesis of -(2-Pyridyl)indoles: A reaction vessel equipped with a magnetic steering bar was charged with compound 1a (0.5 mmol), diphenylacetylene (0.7 mmol), anhydrous CuCl 2 (2 equiv), AP-Mg-Pd(0) (0.030 g), and 3 ml of DMF was added via syringe at room temperature. The reaction mixture was heated at C for 10 h and then cooled to room temperature. The catalyst was separated from the reaction mixture by simple centrifugation. The catalyst was washed with water followed by diethyl ether. It was then dried at room temperature and used as it is for next reaction cycles. The reaction mixture was diluted with water and then extracted with ethyl acetate (5 ml X 3). The combined organic layer was washed with brine solution (10 ml) and then dried over anhydrous a 2 SO 4. After removal of the solvent, the crude product was purified by flash chromatography over silica gel ( mesh) column using hexane/ethyl acetate as an eluent to afford the pure product.. 3

4 Spectral data 2,3-diphenyl-1-(pyridin-2-yl)-1H-indole White solid 1 ; 1 H-MR (300 MHz, CDCl 3 ) : δ = 8.62 (d, 1H J = 5.43 Hz), 7.74 (d, 1H, J = 7.62 Hz), 7.69 (d, 1H, J = 8.24), 7.57 (td, J = 1.98, 7.78 Hz), (m, 4H), (m, 3H), (m, 4H), (m, 2H), 6.82 (d, 1H, J = 8.08 Hz); 13 C-MR (75 MHz, CDCl 3 ) : δ = 151.8, 149.0, 137.5, 137.4,135.9, 134.6, 131.7, 130.9, 130.2, 128.2, 128.0, 127.7, 127.4, 126.1, 123.3, 122.2, 121.5, 121.4, 119.6, 118.2, 111.4; ESI MS (m/z): 347 (M + H) +. H 3 CO OCH 3 2,3-bis(4-methoxyphenyl)-1-(pyridin-2-yl)-1H-indole Light yellow solid 1 ; 1 H-MR (300 MHz, CDCl 3 ): δ = 8.61 (d, 1H, J = 4.73 Hz), (m, 2H), 7.56 (td, 1H, J = 1.98, 7.93 Hz), (m, 3H), (m, 2H), 7.02 (d, 2H, J = 8.69 Hz), 6.88 (d, 2H, J = 8.69 Hz), 6.80 (d, 1H, J = 8.08 Hz), 6.70 (d, J = 8.69 Hz), 3.81 (s, 3H ), 3.74 (s, 3H); 13 C-MR (75 MHz, CDCl 3 ) : δ = 158.6, 157.8, 151.8, 148.8, 137.4, 137.1, 135.3, 131.9, 131.1, 128.3, 126.9, 123.9, 122.9, 122.1, 121.3, 120.4, 119.3, 117.1, 113.6, 113.4, 111.3, 55.0, 54.9; ESI MS (m/z): 407(M + H) +. 4

5 1-(pyridin-2-yl)-2,3-di-p-tolyl-1H-indole white solid 1 ; 1 H-MR (300 MHz, CDCl 3 ): δ = 8.62 (d,1h, J = 4.53 Hz), (m, 2H), 7.57 (td, 1H, J = 1.88, 8.12 Hz), (m, 5H), 7.13 (d, 2H, J = 7.93 Hz), 6.96 (q, 4H, J = 8.20 Hz), 6.80 (d,1h J = 8.12 Hz), 2.36 (s,3h ), 2.27(s, 3H); 13 C-MR (75 MHz, CDCl 3 ) : δ = 151.9, 148.9, 137.5, 137.3, 135.7, 135.5, 131.6, 130.6, 130.0, 128.9, 128.7, 128.3, 123.1, 122.2, 121.4, 121.2, 111.9, 117.7, 111.3, 21.3; ESI MS (m/z): 375(M + H) +. HRMS (m/z): calcd for C 17 H 22 2 : , Found: F F 2,3-bis(4-fluorophenyl)-1-(pyridin-2-yl)-1H-indole White solid; 1 H-MR (300 MHz, CDCl 3 ): δ = 8.61(d, 1H, J = 3.58 Hz), (m, 3H), (m, 5H), (m, 4H), (m, 3H); 13 C-MR (75 MHz, CDCl 3 ) : δ =163.4(d, J F-C = 43.36), (d, J F-C = 41.16), 151.4, 149.2, 137.7, 137.2, 134.8, 132.5, 132.4, 131.7, 130.2, 128.2, 127.5, 123.5, 122.1, 121.6, 119.3, 117.2, (d, J F-C = 21.4), 111.4; ESI MS (m/z): 383 (M + H) + HRMS (m/z): calcd for C 25 H 17 2 F 2 : , Found:

6 3-methyl-2-phenyl-1-(pyridin-2-yl)-1H-indole White solid 1 ; 1H-MR (300 MHz, CDCl 3 ): δ = 8.58 (d, 1H, J = 4.83 Hz), (m, 1H), (m, 1H), 7.51(td, 1H, J = 1.98, 7.62 Hz), (m, 8H), (m, 1H), 2.40 ( s, 3H); 13 C-MR (75 MHz, CDCl 3 ) : δ = 152.1, 148.8, 137.5, 137.1, 135.5, 132.3, 130.2, 129.8, 129.6, 128.4, 128.1, 127.3, 123.1, 122.1, 121.4, 118.6, 112.6, 111.4, 9.5; ESI MS (m/z): 383 (M + H) +. 5-methyl-2,3-diphenyl-1-(pyridin-2-yl)-1H-indole White solid 1 ; 1H-MR (300 MHz, CDCl 3 ): δ = 8.60 (d, 1H, J = 3.81 Hz), 7.60 (d, 1H, J = 8.39 Hz), 7.55 (td, 1H, J = 1.89, 7.93 Hz), 7.50 (s, 1H), (m, 4H), (m, 1H), (m, 4H), (m, 3H), 6.80 (d, 1H, J = 8.08 Hz), 2.45 (s, 3H); 13 C-MR (75 MHz, CDCl 3 ) : δ = 152.0, 148.9, 137.4, 135.9, 134.7, 131.8, 130.8, 130.3, 129.7, 129.0, 127.9, 127.2, 126.0, 124.8, 122.0, 121.3, 119.1, 117.9, 111.2, 21.4; ESI MS (m/z): 361(M + H) +. 6

7 OCH 3 5-methoxy-2,3-diphenyl-1-(pyridin-2-yl)-1H-indole Light yellow solid 1 ; 1H-MR (300 MHz, CDCl 3 ): δ = 8.61 (d, 1H, J = 4.88 Hz), 7.64 (d, 1H, J = 9.00 Hz), 7.54 (d, 1H, J = 1.98, 7.78 Hz), (m, 4H), (m, 1H), (m, 5H), (m, 2H), 6.93 (dd, 1H, J = 2.44, 8.85 Hz), 6.76 (d, 1H, J = 8.08 Hz), 3.85 (s, 3H); 13 C-MR (75 MHz, CDCl 3 ) : δ = 155.4, 151.8, 148.9, 137.5, 136.3, 134.6, 132.5, 131.7, 130.2, 128.7, 128.3, 128.3, 128.0, 127.3, 126.1, 125.1, 122.0, 121.3, 118.1, 113.2, 112.9, 101.2, 55.9; ESI MS (m/z): 377(M + H) +. 5-ethyl-2,3-diphenyl-1-(pyridin-2-yl)-1H-indole White solid; 1H-MR (300 MHz, CDCl 3 ): δ = 8.60 (d, 1H, J = 4.88 Hz), 7.62 (d, 1H, J = 8.54 Hz), (m, 4H), (m, 1H), (m 7H), 6.79 (d, 1H, J = 7.93 Hz), 2.74 (q, 1H, J = 7.54 Hz), (m, 3H); 13 C-MR (75 MHz, CDCl 3 ) : δ = 151.9, 148.9, 137.6, 137.4,135.9, 134.7, 131.8, 130.8, 130.0, 128.4, 128.1, 127.9, 127.2, 126.0, 123.8, 122.0, 121.3, 118.0, 111.3, 29.1, 16.5; ESI MS (m/z): 375(M + H) +. HRMS (m/z): calcd for C 17 H 22 2 : , found:

8 5-(tert-butyl)-2,3-diphenyl-1-(pyridin-2-yl)-1H-indole White solid 1 ; 1H-MR (300 MHz, CDCl 3 ): δ = 8.61 (d, 1H, J = 5.85 Hz), (m, 1H), 7.65 (d, 1H, J = 8.68 Hz), 7.54 (td, 1H, J = 1.70, 7.93 Hz), (m, 5H), (m, 1H), (m, 6H), 6.77 (d, 1H,, J = 8.12 Hz), 1.37 (s, 9H) ; 13 C-MR (75 MHz, CDCl 3 ) : δ = 151.8, 148.9, 137.4, 135.9, 135.5, 134.7, 131.8, 130.8, 130.2, 128.2, 128.0, 127.8, 127.3, 126.0, 121.9, 121.6, 121.3, 118.3, 115.2, 111.4, 34.6, 31.8; ESI MS (m/z): 403 (M + H) +. Cl 5-chloro-2,3-diphenyl-1-(pyridin-2-yl)-1H-indole White solid 1 ; 1H-MR (300 MHz, CDCl 3 ): δ = 8.61 (d, 1H, J = 4.88 Hz), (m, 1H), 7.62 (d, 1H, J = 8.69 Hz), 7.57 (td, 1H, J = 1.98, 7.93 Hz), (m, 4H), (m, 1H), (m, 5H), 6.78 (d, 1H, J = 8.08 Hz); 13 C-MR (75 MHz, CDCl 3 ) : δ =151.4, 149.1, 137.6, 137.0, 135.7, 133.8, 131.1, 130.8, 130.1, 129.3, 128.3, 128.1, 127.1, 126.4, 122.0, 121.8, 119.0, 117.7, 112.7; ESI MS (m/z): 381(M + H) +. 8

9 F 5-fluoro-2,3-diphenyl-1-(pyridin-2-yl)-1H-indole White solid 1 ; 1H-MR (300 MHz, CDCl 3 ): δ = 8.63 (d, 1H, J = 4.73 Hz), (m, 1H), 7.56 (td, 1H, J = 1.87, 7.78 Hz), 7.39 (dd, 1H, J = 2.29, 7.01 Hz), (m, 4H), (m, 1H), (m, 4H), (m, 2H), 7.01(td, 1H, J = 2.44, 6.56 Hz), 6.77(d, 1H, J = 8.08 Hz); 13 C-MR (75 MHz, CDCl 3 ) : δ = (d, d, J F-C = 236 Hz), 157.4, 151.4, 149.0, 137.6, 137.2, 134.0, 133.8, 131.2, 130.7, 130.0, (d, J F-C = 9.8 Hz), 128.3, 128.1, 127.6, 126.3, 122.0, 121.7, 118.0, (d, J F-C = 9.3 Hz), (d, J F-C = 25.7 Hz ortho to F), (d, J F-C = 24.1 Hz); ESI MS (m/z): 365(M + H) +. OCH 3 4-methoxy-2,3-diphenyl-1-(pyridin-2-yl)-1H-indole White solid 1 ; 1H-MR (300 MHz, CDCl 3 ): δ = 8.63 (d, 1H, J = 4.88 Hz), 7.60 (d, 1H, J = 8.69 Hz), 7.55 (td, 1H, J = 1.87, 7.62 Hz), (m, 4H), (m, 2H), (m, 4H), (m, 2H), 6.88 (dd, 1H, J = 2.2, 8.69 Hz), 6.78 (d, 1H, J = 8.08 Hz), 3.84 (s, 3H); 13 C- MR (75 MHz, CDCl 3 ) : δ = 157.4, 152.0, 148.9, 138.2, 137.5, 134.6, 131.8, 130.7, 130.1, 9

10 28.1, 127.9, 127.1, 126.1, 122.6, 122.1, 121.4, 120.2, 118.2, 111.1, 95.3, 55.7; ESI MS (m/z): 377(M + H) + 2-(2,3-diphenyl-1H-indol-1-yl)quinoline White solid 1 ; 1H-MR (300 MHz, CDCl 3 ): δ = 8.17 (d, 1H, J = 8.68 Hz), 7.94 (d, 2H, J = 8.68 Hz), 7.78 (t, 3H, J = 9.34 Hz), 7.57 (t, 1H, J = 7.36 Hz), (m, 5H), (m, 3H), (m, 4H), 6.81 ( d, 1H, J = 8.68 Hz); 13 C-MR (75 MHz, CDCl 3 ) : δ = 151.1, 147.2, 137.4, 135.2, 134.5, 131.8, 130.9, 130.3, 130.0, 128.9, 128,5, 128.2, 128.1, 127.5, 127.4, 126.5, 126.3, 126.2, 123.6, 121.7, 120.5, 119.6, 118.8, 112.0; ESI MS (m/z): 397(M + H) +. 2,3-diphenyl-1-(pyrimidin-2-yl)-1H-indole yellow solid 1 ; 1H-MR (300 MHz, CDCl 3 ): δ = 8.63 (d, 1H, J = 4.73 Hz), 8.13 (d, 1H, J = 8.24 Hz), 7.68 (d,1h, J = 7.78 Hz), (m, 5H), (m, 2H), (m, 5H), 7.08 (t, 1H, J = 4.83 Hz); 13 C-MR (75 MHz, CDCl 3 ) : δ = 158.0, 136.9, 135.9, 134.1, 132.7, 130.3, 130.2, 129.1, 128.1, 127.7, 126.9, 126.3, 123.8, 122.1, 120.2, 119.6, 112.5; ESI MS (m/z): 348M + H) +. 10

11 References 1. Chen, Q. Pang, Y. Sun, X. Li, J. Org. Chem. 2011, 76,

12 H MR and 13 C MR Spectra of 2,3-diphenyl-1-(pyridin-2-yl)-1H-indole 12

13 H MR and 13 C MR Spectra of 2,3-bis(4-methoxyphenyl)-1-(pyridin-2-yl)-1H-indole 13

14 H MR and 13 C MR Spectra of 1-(pyridin-2-yl)-2,3-dip-tolyl-1H-indole 14

15 H MR and 13 C MR Spectra of 2,3-bis(4-fluorophenyl)-1-(pyridin-2-yl)-1H-indole 1 H MR and 13 C MR Spectra of 2-methyl-3-phenyl-1-(pyridin-2-yl)-1H-indole 15

16 6

17 H MR and 13 C MR Spectra of 5-methyl-2,3-diphenyl-1-(pyridin-2-yl)-1H-indole 17

18 H MR and 13 C MR Spectra of 5-methoxy-2,3-diphenyl-1-(pyridin-2-yl)-1H-indole 18

19 H MR and 13 C MR Spectra of 5-ethyl-2,3-diphenyl-1-(pyridin-2-yl)-1H-indole 19

20 H MR and 13 C MR Spectra of 5-tert-butyl-2,3-diphenyl-1-(pyridin-2-yl)-1H-indole 20

21 H MR and 13 C MR Spectra of 5-Chloro-2,3-diphenyl-1-(pyridin-2-yl)-1H-indole 21

22 H MR and 13 C MR Spectra of 5-fluoro-2,3-diphenyl-1-(pyridin-2-yl)-1H-indole 22

23 H MR and 13 C MR Spectra of 4-methoxy-2,3-diphenyl-1-(pyridin-2-yl)-1H-indole 23

24 H MR and 13 C MR Spectra of 2-(2,3-diphenyl-1H-indol-1-yl)quinoline 24

25 H MR and 13 C MR Spectra of 2,3-diphenyl-1-(pyrimidin-2-yl)-1H-indole 25

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