## 2 Experimental
### General Procedure for Synthesis of N-methyl-3-aryl imidazole (5a-5j) (Route 2)  
Under nitrogen atmosphere, to a mixture of \(N\)-methyl-3-iodoidazole **4** (0.3 g, 1.16 mmol) and aryl boronic acid (1.74 mmol) in DMF, NaHCO\({}_{3}\) (0.2 g, 3.4 mmol) in water was added. To this reaction, mixture Pd (PPh\({}_{3}\))\({}_{4}\) (0.1 g, 0.1 mmol) was added and refluxed with vigorous stirring for 10-14 h. The solvent of the reaction mixture was then evaporated, and the crude obtained was dissolved in ethyl acetate; the organic phase was washed with brine solution, dried over sodium sulfate, and the solvent was removed under vacuum to give crude compound. The crude mixture is purified by silica gel (60-120 mesh) column chromatography using 30% ethyl acetate in hexane as eluent to afford the respective products N-methyl-3-aryl indazole (5a-5j). Spectral Data of Compounds (3a-3j) and (5a-5j)  
_3-Phenyl-1\(H\)-indazole (3a):_ m.p. 114-116 \({}^{\circ}\)C; IR (KBr, \(\upsilon_{\max}\), cm\({}^{-1}\)): 3691 (OH str), 3440 (b,NH str), 2991 (Ar=CH str), 2897 (CH str), 1601, 1545, 1498 (Ar C=C str), 1450 (C=N str), 1233 (N-N str); NMR: \({}^{1}\)H (500 MHz, CDCl3): \(\delta\) = 11.18 (b, 1H), 8.08-8.04 (m, 3H), 7.58 (t, \(J\) = 7.5, 2H), 7.49-7.46 (m, 1H), 7.43-7.37 (m, 2H), 7.29-7.25 (m, 1H); \({}^{13}\)C-NMR: (125 MHz, DMSO): \(\delta\) = 145.8, 141.7, 133.6, 128.9, 128.2, 127.7, 126.8, 121.4, 121.1, 121.0, 110.2; \(m\)/z (ESI-MS) 195.23 (M + H)\({}^{+}\). _3-(Naphthalene-1-yl)-1\(H\)-indazole (3b):_ m.p. 136-138 \({}^{\circ}\)C; IR (KBr, \(\upsilon_{\max}\), cm\({}^{-1}\)): 3446 (b,NH str), 2929 (Ar=CH str), 1595, 1581, 1506 (Arc=C str), 1418 (C=N str), 1246 (N-N str);NMR: \({}^{1}\)H (500 MHz, CDCl3): \(\delta\) = 12.25 (b, 1H), 8.32-8.31 (m, 1H), 8.01-7.98 (m, 2H), 7.79-7.67 (m, 2H), 7.57-7.52 (m, 2H), 7.48-7.39 (m, 2H), 7.21 (t, \(J\) = 6.7, 1H), 6.93-6.92 (m, 1H). \({}^{13}\)C-NMR (125 MHz, CDCl3): \(\delta\) = 143.4, 134.1, 131.9, 131.3, 128.8, 128.2, 128.1, 126.7, 126.4, 126.3, 126.1, 125.4, 121.9, 121.3, 110.9: \(m\)/z (ESI-MS) 245.05 (M + H)\({}^{+}\). _3-(4-Fluorophenyl)-1\(H\)-indazole (3c):_ m.p. 112-113 \({}^{\circ}\)C; IR (KBr, \(\upsilon_{\max}\), cm\({}^{-1}\)): 3406 (NH str), 3078 (ArH str), 2924 (ArH str), 1625, 1563 (Arc=C str), 1440 (C=N str), 1370 (C=N str), 814 (C-F str); \({}^{1}\)H NMR (300 MHz, CDCl3): \(\delta\) 8.05 (m, 3H, ArH), 7.45 (m, 2H, ArH), 7.25 (m, 1H, ArH); 7.21 (m, 2H, ArH); \({}^{13}\)C NMR (75 MHz, CDCl3): \(\delta\) = 151.0, 147.2, 138.5, 130.1, 128.8, 126.2, 124.4, 122.1, 121.7, 113.8; \(m\)/z (ESI-MS) 213.27 (M + H)\({}^{+}\). _3-(Pyridin-4-yl)-1\(H\)-indazole (3d):_ m.p. 101-103 \({}^{\circ}\)C; IR (KBr, \(\upsilon_{\max}\), cm\({}^{-1}\)): 3430 (NH str), 3032 (ArCH str), 1584, 1549, 1491(Arc=C str), 1373 (C=N str), 1211 (N-N str); \({}^{1}\)H NMR (300 MHz, CDCl3): \(\delta\) 7.73-7.62(m, 4H, Ar-H), 7.62 (d, \(J\) = 8 Hz, 2H, Ar-H); 7.45 (d, \(J\) = 9 Hz, 2H, Ar-H); \({}^{13}\)C NMR (125 MHz, CDCl\({}_{3}\)); \(\delta\) = 148.8, 143.6, 138.5, 130.1, 128.8, 126.2, 124.4, 122.1, 121.7, 112.3; \(m\)/z (ESI-MS) 196.26 (M + H)\({}^{+}\). _3-(Pyridin-3-yl)-1H-indazole_ **(3e):** m.p. 184-186 \({}^{\circ}\)C; IR (KBr, \(\upsilon_{\max}\), cm\({}^{-1}\)): 3409 (b, NH str), 3066 (ArCH str), 1589, 1560, 1512(ArC= c str), 1340 (C=N str), 1216 (N-N str); \({}^{1}\)H NMR (300 MHz, CDCl\({}_{3}\)): \(\delta\) 10.92 (s, 1H, NH), 9.25 (s, 1H, ArH), 8.65 (d, 1H, \(J\) = 7.5, Ar-H), 8.42 (d, 1H, \(J\) = 8.4 Hz, ArH); 8.05 (d, \(J\) = 7.5 Hz, 1H, Ar-H) 7.22-7.64 (m, 4H, ArH); \({}^{13}\)C NMR (125 MHz, CDCl\({}_{3}\)): \(\delta\) = 148.5, 139.6, 139.2, 128.8, 127.5, 126.2, 125.2, 124.4, 124.3, 123.0, 122.6, 122.2; \(m\)/z (ESI-MS) 196.26 (M + H)\({}^{+}\). _3-(4-Methoxyphenyl)-1H-indazole_ **(3f):** m.p.