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CAS No. : | 874-10-2 | MDL No. : | MFCD05663805 |
Formula : | C8H8N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BJZAXTJBEBNEDL-UHFFFAOYSA-N |
M.W : | 132.16 | Pubchem ID : | 327957 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280 | UN#: | N/A |
Hazard Statements: | H302-H317 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With hydrogen bromide In ethanol; water at 90℃; for 26 h; | 2-amino-3-methylpyridine (10 g, 92.5 mmol) and 2-bromo-1,1-diethoxyethane (36.4 g, 185 mmol) were dissolved in ethanol (100 mL) Then, 48percent aqueous hydrogen bromide solution (9 mL) was slowly added dropwise to the reaction solution. After the reaction system was heated to 90 ° C for 26 hours, LC-MS detection reaction has ended, And then cooled to room temperature. The first reaction in the system of ethanol decompression distillation, The excess hydrobromic acid in the reaction was neutralized with excess saturated sodium bicarbonate water (100 mL) and sodium bicarbonate solids (15 g). The remaining mixture was extracted with ethyl acetate (200 mL x 3) All organic phases were then mixed and washed once with deionized water (100 mL) and saturated brine (100 mL) Dried over anhydrous sodium sulfate, Press the steam to remove the solvent. The remaining mixture was purified by silica gel column chromatography (eluent: dichloromethane / methanol = 0-10percent), To give 8-methyl-imidazo [1,2-a] pyridine (12 g, yield 98percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With sodium chloride; sodium hydrogencarbonate In water | EXAMPLE IV 8-METHYLIMIDAZO[1,2-A]PYRIDINE To a mixture of chloroacetaldehyde [25.4 mL (0.2 mole) of a 50percent aqueous solution]and 18.8 g (0.2 mole) of 2-amino-3-methylpyridine in 150 mL of water was added 16.8 g (0.2 mole) of sodium bicarbonate. After being stirred at 25° C. for 3 days, the mixture was acidified with concentrated hydrochloric acid and stirred an additional 30 minutes. After the pH was adjusted to 10 by addition of sodium hydroxide, the mixture was saturated with sodium chloride and extracted with ether. The ether extracts were dried and concentrated to give 16.3 g (62percent) of a liquid residue, bp 68°-70° C. at 0.1 Torr. Imidazo[1,2-a]pyridine, bp 61°-66° C. at 0.1 Torr., was prepared in an analogous manner. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10% | Stage #1: at -30℃; Stage #2: at -30 - 20℃; |
Preparation of ethyl imidazopyridine propenoate (According to the Literature Method: Chezal, J. M. and al. J. Org. Chem. 2001, 66, 6576-6584).Ethyl azidoacetate (1.81 g, 14.0 mmol) was added dropwise at -30° C. to a stirred solution containing sodium (0.20 g, 8.70 mmol) in dry ethanol (10 mL). To this solution was added dropwise a solution of aldehyde 4 (1.00 mmol) in dry ethanol (8 mL). The reaction mixture was returned back room temperature and stirred for 3 h (CAUTION: an exothermic reaction can take place, with gas expansion). The solution was poured into aqueous saturated ammonium chloride solution (30 mL) and then extracted with CH2Cl2. The organic layers were dried (Na2SO4), filtered and evaporated in vacuo. The crude product was purified by chromatography using CH2Cl2 as eluent to afford the azide derivative 6; Example 35 Ethyl α-azido-β-(imidazo[1,2-a]pyridin-8-yl)propenoate (6a) From 4a (yield: 10percent); mp: 150-152° C.; IR (KBr) 2100, 1700, 1600, 1280 cm-1; 1H NMR (400 MHz, CDCl3) δ 1.41 (t, 3H, J=7 Hz), 4.39 (q, 2H, J=7 Hz), 6.83 (t, 1H, J=7 Hz), 7.57 (d, 1H, J=1 Hz), 7.61 (d, 1H, J=1 Hz), 7.76 (s, 1H), 8.06 (dd, 1H, J=7, 1 Hz), 8.17 (dd, 1H, J=7, 1 Hz). MS m/z 257 (M+, 1), 229 (61), 183 (100), 155 (31), 129 (23), 104 (14). Further elution gave 8-methylimidazo[1,2-a]pyridine (yield: 10percent-Kaiser, C. and al. J. Med. Chem. 1992, 35, 4415-4424). |
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