5-BROMO-3-IODO (1H)INDAZOLE

General procedure: 3-Iodoindazoles were obtained by direct iodination of commercial indazoles by the method previously described by Bocchi [28] with slight modifications. A solution of 1H-indazole (3 g, 25.4 mmol), iodine (12.7 g, 50.03 mmol) and potassium hydroxide (5.34 g, 95.25 mmol)in DMF (7 mL) was stirred for 3 h at room temperature. The reaction was quenched by dilution with saturated solution of sodium bisulfite (150 mL) and a precipitated was formed. The precipitated was filtered over vacuum and washed with water (3 × 30 mL). The solid was left to dry at 30 °C in a vacuum oven overnight obtaining 6.17 g of a pale yellow solid. Yield: 100percent; m.p.: 136–138 °C (lit.:[36] 134–136 °C); IR (KBr) ν (cm−1): 3086 (NH); 424 (C-I). 1H-NMR δ (ppm): 13.50 (1H, s, H-1); 7.55(1H, d, J = 8.6 Hz, H-7); 7.45–7.40 (2H, m, H-6 and H-4); 7.19 (1H, dd, J = 7.5 Hz, H-5). 13C-NMR δ(ppm): 140.41; 127.22; 126.79; 121.23; 120.39; 110.51; 93.49; HRMS calculated for C7H5IN2: 243.9497, Found: 243.9499.3-Iodo-1H-indazole (1a). 3-Iodoindazoles were obtained by direct iodination of commercial indazoles by the method previously described by Bocchi [28] with slight modifications. A solution of 1H-indazole(3 g, 25.4 mmol), iodine (12.7 g, 50.03 mmol) and potassium hydroxide (5.34 g, 95.25 mmol) in DMF(7 mL) was stirred for 3 h at room temperature. The reaction was quenched by dilution with saturated solution of sodium bisulfite (150 mL) and a precipitated was formed. The precipitated was filtered over vacuum and washed with water (3 30 mL). The solid was left to dry at 30 °C in a vacuum oven overnight obtaining 6.17 g of a pale yellow solid. Yield: 100percent; m.p.: 136–138 °C (lit.: [36] 134–136 °C)To a solution of 5-bromo-1H-indazole (5.0 g, 25.4 mmol, 1.0 eq.) in anhydrous DMF (15.0 mL) was added KOH (4.3 g, 76.1 mmol, 3.0 eq.) and ‘2 (12.9 g, 50.75 mmol, 2.0 eq.) under nitrogen. The mixture was stirred at rtrt for 2 h, then diluted with ice water, extracted with EA (50 mL x 2). The combined organic layers were washed with aqueous Na2S2O3 solution and brine, dried over anhydrous Na2SO4 and concentrated in vacuum to provide 5-bromo-3-iodo-1H-indazole (8.0 g, 97.9percent) which was used in the next step without further purification.Step 1 - Synthesis of 5-bromo-3-iodo-lH-indazole KOH (4.27 g, 76.13 mmol) was added into a solution of 5-bromo-lH-indazole (5.0 g, 25.38 mmol) and IStep 1 - Synthesis of 5-bromo-S-iodo-lH-indazole KOH (4.27 g, 76.13 mmol) was added into a solution of 5-bromo-lH-indazole (5.0 g, 25.38 mmol) and ITo a solution of 5-bromoindazole 1 (2.53 g, 12.84 mmol) in DMF (20 mL) was added I

Molecular Weight:322.93
XLogP3:2.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:321.86026
Monoisotopic Mass:321.86026
Topological Polar Surface Area:28.7
Heavy Atom Count:11
Complexity:155
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes