## 2 Experimental
### General Procedure for Synthesis of N-methyl-3-aryl imidazole (5a-5j) (Route 2)
85-87 \({}^{\circ}\)C; IR (KBr, \(\upsilon_{\max}\), cm\({}^{-1}\)): 3429 (NH str), 3054 (ArH str), 2927 (CH str), 1583, 1487 (ArC= c str), 1438 (C=N str), 1375 (C=N str), 1169 (C-O-C str); \({}^{1}\)H NMR (300 MHz, CDCl\({}_{3}\)): \(\delta\) 8.26 (s, 1H, NH), 8.03 (d, 1H, \(J\) = 8.0, ArH), 7.85 (dd, 2H, \(J\) = 10.5, ArH), 7.46 (m, 2H, ArH); 7.22 (m, 1H, ArH), 7.03 (dd, 2H, \(J\) = 10.4, ArH); \({}^{13}\)C NMR (75 MHz, CDCl\({}_{3}\)): \(\delta\) = 159.6, 145.7, 141.8, 128.9, 126.6, 126.2, 121.1, 121.1, 114.4, 110.3, 55.3; \(m\)/z (ESI-MS) 225.31 (M + H)\({}^{+}\). _3-(4-(Methylthio)phenyl)-1H-indazole_ **(3g):** m.p. 123-125 \({}^{\circ}\)C; IR (KBr, \(\upsilon_{\max}\), cm\({}^{-1}\)): 3378 (NH str), 3052 (ArH str), 2925 (CH str), 1600, 1521 (ArC= c str), 1346 (C=N str), 1106 (C-S-C str); \({}^{1}\)H NMR (300 MHz, CDCl\({}_{3}\)): \(\delta\) 8.16 (s, 1H, NH), 7.92 (d, 2H, \(J\) = 7.5, ArH), 7.52 (d, 1H, \(J\) = 8.4, ArH), 7.38-7.51 (m, 4H, ArH); 7.23 (s, 1H, ArH), 2.45 (s, 3H, CH\({}_{3}\)); \({}^{13}\)C NMR (125 MHz, CDCl\({}_{3}\)): \(\delta\) = 160.0, 145.7, 141.8, 134.7, 129.9, 126.8, 121.4, 121.0, 120.2, 114.2, 112.9, 110.3, 55.3; \(m\)/z (ESI-MS) 241.30 (M + H)\({}^{+}\). _3-(2-Methoxyphenyl)-1H-indazole_ **(3h):** m.p. 115-116 \({}^{\circ}\)C; IR (KBr, \(\upsilon_{\max}\), cm\({}^{-1}\)): 3325 (b, NH str), 3025 (ArCH str), 2921 (CH str), 1659, 1513, 1437(ArC= c str), 1370 (C=N str), 1212 (N-N str), 1148 (C-O-C str); \({}^{1}\)H NMR (300 MHz, CDCl\({}_{3}\)): \(\delta\) 7.81 (s, 1H, NH), 7.72 (d, 1H, \(J\) = 7.5 Hz, ArH), 7.52 (d, \(J\) = 8.5 Hz, 1H, Ar-H) 7.42 (m, 2H, ArH); 7.21 (m, 1H, ArH), 7.09 (m, 1H, ArH), 7.02 (d, 1H, \(J\) = 10.2 Hz, ArH), 3.8 (s, 3H, OCH\({}_{3}\)).\({}^{13}\)C NMR (125 MHz, CDCl\({}_{3}\)): \(\delta\) = 157.3, 143.0, 141.4, 131.4, 129.7, 126.3, 122.2, 122.0, 120.9, 120.5, 111.4, 110.4, 55.4; \(m\)/z (ESI-MS) 225.30 (M + H)\({}^{+}\). _4-(1H-indazol-3-yl)-phenol_**(3i):** m.p. 121-123 \({}^{\circ}\)C; IR (KBr, \(\upsilon_{\max}\), cm\({}^{-1}\)): 3414 (OH str), 3315 (b,NH str), 2925 (Ar=CH str), 1651, 1560, 1505(ArC= c str), 1414 (C=N str), 1219 (N-N str), 1093 (C-O str); \({}^{1}\)H NMR (300 MHz, CDCl\({}_{3}\)): \(\delta\) 13.12 (s, 1H, PhOH), 9.62 (s, 1H, NH), 8.01 (d, 1H, \(J\) = 8.4 Hz, ArH), 7.82 (d, \(J\) = 7.5 Hz, 2H, Ar-H), 7.49 (d, \(J\) = 10.2, 1H, ArH), 7.39 (d, \(J\) = 10.4, 1H, ArH), 7.22 (d, \(J\) = 8.0 Hz, 1H, ArH), 6.96 (m, 2H, ArH); \({}^{13}\)C NMR (75 MHz, CDCl\({}_{3}\)): \(\delta\) = 158.4, 151.4, 148.6, 138.8, 132.5, 134.8, 128.7, 125.9, 122.1, 113.5, 104.1; \(m\)/z (ESI-MS) 211.30 (M + H)\({}^{+}\). _4-(1H-indazol-3-yl)-N,N-dimethylbenzamide_ **(3j):** m.p. 116-117 \({}^{\circ}\)C; IR (KBr, \(\upsilon_{\max}\), cm\({}^{-1}\)): 3456 (b, NH str), 2933 (Ar=CH str), 2835 (CH str), 1817 (CO str), 1649, 1530, 1488(ArC= c str), 1386(C=N str), 1210 (N-N str); \({}^{1}\)H NMR (500 MHz, CDCl\({}_{3}\)): \(\delta\) 9.86 (s, 1H, NH), 8.09 (m, 3H, ArH), 7.61 (m, 3H, Ar-H), 7.45 (d, \(J\) = 10.5 Hz, 1H, ArH); 7.28 (s, 1H, ArH), 3.12 (s, 6H, CH\({}_{3}\)); \({}^{13}\)C NMR (100 MHz, CDCl\({}_{3}\)): \(\delta\) = 166.3, 145.7, 135.2, 132.2, 130.4, 128.7, 128.6, 128.1, 127.9, 127.3, 126.5, 114.1, 36.4; \(m\)/z (ESI-MS) 266.35 (M + H)\({}^{+}\). _1-Methyl-3-phenyl-1H-indazole_ **(5a):** m.p. 76-78 \({}^{\circ}\)C; IR (KBr, \(\upsilon_{\max}\), cm\({}^{-1}\)): 3429 (NH str),CH\({}_{3}\)); \({}^{13}\)C NMR (100 MHz, CDCl\({}_{3}\)): \(\delta\) = 162.8, 145.2, 139.1, 136.7, 132.2, 128.9, 128.7, 128.2, 123.4, 119.5, 117.6, 110.5, 35.2; _m/z_ (ESI-MS) 227.31 (M + H)\({}^{+}\). _1-Methyl-3-(pyridin-4-yl)-1H-inadazole_ **(5d)**: m.p.