5-BROMO-1H-INDAZOLE-3-CARBOXYLIC ACID synthesis
- Product Name:5-BROMO-1H-INDAZOLE-3-CARBOXYLIC ACID
- CAS Number:1077-94-7
- Molecular formula:C8H5BrN2O2
- Molecular Weight:241.04
4498-67-3
1077-94-7
Step 1: Indazole-3-carboxylic acid (CXXXI) (1.0 g, 6.16 mmol) was suspended in glacial acetic acid (60 mL) and heated to 120 °C until a clear solution was formed. The solution was then cooled to 90 °C. A solution of bromine (0.633 mL, 12.33 mmol) in glacial acetic acid (2 mL) was slowly added dropwise to the solution at 90 °C. After addition, the reaction continued to be heated at 90 °C for 16 hours. After completion of the reaction, the solution was cooled to room temperature and poured into ice water and stirred at room temperature for 15 minutes. The precipitated solid was filtered, washed with cold water and dried under vacuum at room temperature to afford 5-bromo-1H-indazole-3-carboxylic acid (CXXXII) as a white solid (1.30 g, 5.39 mmol, 87.5% yield). The product was characterized by 1H NMR (DMSO-d6): δ 13.95 (s, 1H), 13.18 (br s, 1H), 8.21 (d, J = 1.2 Hz, 1H), 7.65 (d, J = 7.0 Hz, 1H), 7.56 (dd, J = 7.0, 1.2 Hz, 1H); ESIMS m/z 242.0 ([M + H]+. (calculated value C8H4BrN2O2).
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1077-94-7
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Yield:1077-94-7 87.5%
Reaction Conditions:
with bromine;acetic acid at 90 - 120; for 16 h;
Steps:
1
Step 1
A suspension of indazole-3-carboxylic acid (CXXXI) (1.0 g, 6.16 mmol) in glacial acetic acid (60 mL) was heated at 120° C. to get a clear solution.
The solution was cooled to 90° C. A solution of bromine (0.633 mL, 12.33 mmol) in glacial acetic acid (2 mL) was added slowly to the solution while heating at 90° C.
The solution was further heated 16 h at 90° C.
The solution was cooled to room temperature, poured into ice water and further stirred at room temperature for 15 min.
The solids formed were filtered, washed with cold water and dried under vacuum at room temperature to get 5-bromo-1H-indazole-3-carboxylic acid (CXXXII) as a white solid (1.30 g, 5.39 mmol, 87.5% yield).
1H NMR (DMSO-d6) δ ppm 13.95 (s, 1H), 13.18 (br s, 1H), 8.21 (d, J=1.2 Hz, 1H), 7.65 (d, J=7.0 Hz, 1H), 7.56 (dd, J=7.0, 1.2 Hz, 1H); ESIMS found for C8H4BrN2O2 m/z 242.0 (M+H).
References:
US2015/266825,2015,A1 Location in patent:Paragraph 1359; 1360
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1077-94-7
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1077-94-7
185 suppliers
$11.00/250mg