6-broMo-3-iodoH-iMidazo[1,2-a]pyridine Chemical Properties

Melting point:

209℃

Density 

2.41

storage temp. 

2-8°C(protect from light)

pka

2.45±0.50(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C7H4BrIN2/c8-5-1-2-7-10-3-6(9)11(7)4-5/h1-4H

InChIKey

VADGFPDSVWQCHR-UHFFFAOYSA-N

SMILES

C12=NC=C(I)N1C=C(Br)C=C2

6-broMo-3-iodoH-iMidazo[1,2-a]pyridine Usage And Synthesis

Synthesis

GENERAL STEPS: 6-Bromoimidazo[1,2-a]pyridine (721 mg, 3.66 mmol) was dissolved in 20 mL of acetonitrile (ACN), followed by the addition of N-iodosuccinimide (988 mg, 4.39 mmol). The reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was removed by rotary evaporator under reduced pressure. The residue was dissolved with dichloromethane (CH2Cl2) and washed sequentially with 10% aqueous sodium hydroxide (NaOH), saturated aqueous sodium thiosulfate (Na2S2O3) and deionized water. The organic layer was dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure to afford the target compound 6-bromo-3-iodoimidazo[1,2-a]pyridine as a white solid (1.18 g, 96% yield) with a melting point of 209 °C. The product was analyzed by ATR-IR showing characteristic absorption peaks (cm-1): 3024, 1516, 711, 698.1H NMR (400 MHz, CDCl3) δ: 7.29 (dd, J = 9.6, 1.8 Hz, 1H), 7.51 (d, J = 9.6 Hz, 1H), 7.70 (s, 1H), 8.26-8.28 (m, 1H). 1H).13C NMR (100.6 MHz, CDCl3) δ: 61.4, 108.4, 118.6, 126.4, 128.6, 128.6, 141.1, 146.5.High-resolution mass spectrometry (HRMS, EI) m/z calculated value of C7H4BrIN2 [M+H]+: 322.8675, measured value: 322.8678.

References

[1] Tetrahedron, 2011, vol. 67, # 37, p. 7128 - 7138
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 7, p. 2455 - 2466
[3] Patent: WO2008/14219, 2008, A2. Location in patent: Page/Page column 45
[4] Patent: WO2013/147711, 2013, A1. Location in patent: Page/Page column 248
[5] Patent: US2014/371199, 2014, A1. Location in patent: Paragraph 0852

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