1-Boc-3-iodoindazole synthesis
- Product Name:1-Boc-3-iodoindazole
- CAS Number:290368-00-2
- Molecular formula:C12H13IN2O2
- Molecular Weight:344.15
24424-99-5
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290368-00-2
1. 3-Iodo-1H-indazole (0.2 g, 0.82 mmol), di-tert-butyl dicarbonate (0.2 g, 0.92 mmol) and triethylamine (1 mL) were mixed and placed under ultrasonic radiation for 10 minutes. 2. After completion of the reaction, the reaction mixture was neutralized with 1 M HCl solution. 3. The neutralized solution was extracted using dichloromethane (3 x 30 mL). 4. The organic layers were combined and dried over anhydrous sodium sulfate. 5. Vacuum remove the solvent to give the pure product 3-iodo-1H-indazole-1-carboxylic acid tert-butyl ester as light yellow crystals. Yield: 100%; Melting point: 93-95°C; IR (KBr) ν (cm^-1): 1728 (C=O); 1150 (C-O); 424 (C-I). 1H-NMR (CDCl3) δ (ppm): 8.09 (1H, d, J=8.5 Hz, H-7); 7.55 (1H, t, J=7.8 Hz, H-4); 7.46 (1H, d, J=7.9 Hz, H-6); 7.33 (1H, t, J=7.6 Hz, H-5); 1.71 (9H, s, CH3). 13C-NMR (CDCl3) δ (ppm): 148.35; 139.59; 130.17; 129.98; 124.21; 121.96; 114.56; 102.95; 85.48; 28.18. HRMS (ESI) m/z calculated value C12H13IN2O2 [M+H]+: 344.0022, measured value: 344.0016. For the synthesis of tert-butyl 3-iodo-5-nitro-1H-indazole-1-carboxylate (2b): 1. 3-iodo-5-nitro-1H-indazole (0.2 g, 0.69 mmol), di-tert-butyl dicarbonate (0.17 g, 0.78 mmol) and triethylamine (1 mL) were used as raw materials, and the same procedure as above was followed. 2. 0.27 g of pure product as a pale yellow solid was obtained. Yield: 100%; Melting point: 144-145 °C; IR (KBr) ν (cm^-1): 1744 (C=O); 1528 (NO2).
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Yield:290368-00-2 100%
Reaction Conditions:
with triethylamineSonication;
Steps:
tert-Butyl 3-iodo-1H-indazole-1-carboxylate (2a).
A mixture of 3-iodo-1H-indazole (0.2 g, 0.82 mmol), ditert-butyldicarbonate (0.2 g, 0.92 mmol) and triethylamine (1 mL) were put under ultrasonic irradiation for 10 min. The resulted solution was neutralized using HCl 1M and then extracted with dichloromethane (3 × 30 mL). The combined organic layers were dried with anhydrous sodium sulfate and removal of the solvent under vacuum afforded a pure product as a pale yellow crystals.Yield: 100%; m.p.: 93-95 °C; IR (KBr) ν (cm-1): 1728 (C=O); 1150 (C-O); 424 (C-I). 1H-NMR (CDCl3) δ(ppm): 8.09 (1H, d, J = 8.5 Hz, H-7); 7.55 (1H, t, J = 7.8 Hz, H-4); 7.46 (1H, d, J = 7.9 Hz, H-6); 7.33 (1H,t, J = 7.6 Hz, H-5); 1.71 (9H, s, CH3). 13C-NMR δ (ppm): 148.35; 139.59; 130.17; 129.98; 124.21; 121.96;114.56; 102.95; 85.48; 28.18; HRMS calculated for C12H13IN2O2: 344.0022, Found: 344.0016.tert-Butyl 3-iodo-5-nitro-1H-indazole-1-carboxylate (2b). Prepared from 3-iodo-5-nitro-1H-indazole (0.2g, 0.69 mmol), di-tert-butyldicarbonate (0.17 g, 0.78 mmol) and triethylamine (1 mL) to give 0.27 g ofa pale yellow solid. Yield: 100%; m.p.: 144-145 °C; IR (KBr) ν (cm-1): 1744 (C=O); 1528 (NO2tert-Butyl 3-iodo-1H-indazole-1-carboxylate (2a). A mixture of 3-iodo-1H-indazole (0.2 g, 0.82 mmol),di-tert-butyldicarbonate (0.2 g, 0.92 mmol) and triethylamine (1 mL) were put under ultrasonicirradiation for 10 min. The resulted solution was neutralized using HCl 1M and then extractedwith dichloromethane (3 30 mL). The combined organic layers were dried with anhydrous sodiumsulfate and removal of the solvent under vacuum afforded a pure product as a pale yellow crystals.Yield: 100%; m.p.: 93-95 °C; IR (KBr) (cm1): 1728 (C=O); 1150 (C-O); 424 (C-I). 1H-NMR (CDCl3) (ppm): 8.09 (1H, d, J = 8.5 Hz, H-7); 7.55 (1H, t, J = 7.8 Hz, H-4); 7.46 (1H, d, J = 7.9 Hz, H-6); 7.33 (1H,t, J = 7.6 Hz, H-5); 1.71 (9H, s, CH3). 13C-NMR (ppm): 148.35; 139.59; 130.17; 129.98; 124.21; 121.96;114.56; 102.95; 85.48; 28.18; HRMS calculated for C12H13IN2O2: 344.0022, Found: 344.0016.
References:
Vera, Gonzalo;Diethelm, Benjamín;Terraza, Claudio A.;Recabarren-Gajardo, Gonzalo [Molecules,2018,vol. 23,# 8,art. no. 2051]
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