| Identification | More | [Name]
5-CHLORO-2-IODOPYRIDINE | [CAS]
244221-57-6 | [Synonyms]
5-CHLORO-2-IODOPYRIDINE
2-IODO-5-CHLOROPYRIDINE | [EINECS(EC#)]
1308068-626-2 | [Molecular Formula]
C5H3ClIN | [MDL Number]
MFCD07368864 | [Molecular Weight]
239.44 | [MOL File]
244221-57-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
85-87 °C(Solv: hexane (110-54-3)) | [Boiling point ]
237.3±20.0 °C(Predicted) | [density ]
2.052±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [form ]
Solid | [pka]
-0.44±0.10(Predicted) | [Appearance]
Off-white to light brown Solid | [Water Solubility ]
Slightly soluble in water. | [Sensitive ]
Light Sensitive | [CAS DataBase Reference]
244221-57-6(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
It is applied in an efficient preparation of indolizines through a tandem palladium-catalyzed cross-coupling reaction and cycloisomerization and also in the synthesis, and structure-activity relationships of 2-aminoquinazoline derivatives as a novel class of metabotropic glutamate receptor 5 negative allosteric modulators. | [Synthesis]
General procedure for the synthesis of 5-chloro-2-iodopyridine from 2-bromo-5-chloropyridine:
1. Preparation: acetyl chloride (11.05 mL, 0.155 mol) was slowly added to a solution of 2-bromo-5-chloropyridine (20.0 g, 0.103 mol) in acetonitrile (120 mL) followed by sodium iodide (23.3 g, 0.155 mol). The reaction mixture was heated to reflux and a drying tube was fitted for 3 hours.
2. Post-treatment: after completion of the reaction, the mixture was cooled in an ice bath and saturated aqueous potassium carbonate solution was slowly added to alkalize the reaction solution. The reaction mixture was extracted with ethyl acetate (2 x 100 mL). The organic layers were combined, washed with saturated aqueous sodium sulfite (200 mL), dried over anhydrous magnesium sulfate and subsequently concentrated under reduced pressure.
3. Repeat the reaction: to ensure that the reaction was complete, the residue was subjected to the same reaction and post-treatment steps again. The target compound 5-chloro-2-iodopyridine (18.71 g, 75% yield) was finally obtained as a brown solid.
4. Characterization: 1H NMR (CDCl3, 400 MHz) δ 7.30 (1H, dd), 7.65 (1H, d), 8.35 (1H, d); LRMS (APCI+) m/z 240 [MH+]. | [References]
[1] Tetrahedron, 2004, vol. 60, # 51, p. 11869 - 11874
[2] Patent: WO2007/96763, 2007, A2. Location in patent: Page/Page column 52
[3] Patent: WO2007/15162, 2007, A1. Location in patent: Page/Page column 91
[4] Patent: US2011/306592, 2011, A1. Location in patent: Page/Page column 92 |
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