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

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

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

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