2549-19-1|Ethyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate| Ambeed

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Quality Control of [ 2549-19-1 ] Purity: 97% SDS Specification

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Product Details of [ 2549-19-1 ]

CAS No. :	2549-19-1
Formula :	C₁₁H₁₂N₂O₂
M.W :	204.23
SMILES Code :	CCOC(=O)C1=C(C)N=C2C=CC=CN12
MDL No. :	MFCD00139509
InChI Key :	FLAQFBICEAEEOA-UHFFFAOYSA-N
Pubchem ID :	743829

Safety of [ 2549-19-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 2549-19-1 ]

* 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.

Downstream synthetic route of [ 2549-19-1 ]

[ 2549-19-1 ] Synthesis Path-Downstream 1~35

1
[ 504-29-0 ]
ethyl 2-bromoacetoacetate [ No CAS ]
[ 2549-19-1 ]

Yield	Reaction Conditions	Operation in experiment
	In water; at 80℃; for 0.5h;Green chemistry;	General procedure: To a round bottom flask containing 1,3-diketones/β-keto esters/aryl ketones (1.05 mmol) and water (5 mL) was added NBS (1.2 mmol) and mixture was allowed to stir at 80 C for 30 min. Subsequently, 2-aminopyridine/2-aminopyrimidine/2-aminothiazole (1.0 mmol) was added and reaction mixture was further heated to 80 C for 30 min. After completion of reaction (checked by TLC), it was allowed to cool to room temperature and then the mixture was poured into 10 mL of sodium carbonate solution. The reaction mixture was extracted with ethyl acetate (3 x 20 mL). The combined organic layer was washed with water, saturated brine solution, dried over anhydrous Na2SO4 and concentrated in vaccuo. The resulting crude product was purified by silica gel column chromatography with petroleum ether-ethyl acetate to give corresponding imidazo[1,2-a]pyridine/imidazo[1,2-a]pyrimidine/imidazo[2,1-b]thiazole. B. Characterization dataEthyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate 3a (Table 2, entry 1)1: Isolated yield 91%, White solid, mp 66-68 C (lit. mp 68-70 C). IR (KBr, cm-1) vmax 3410, 3145, 2999, 1678, 1595, 1490, 1411, 1296, 1222, 1094, 850, 761. 1H NMR (400 MHz, CDCl3) δ ppm 9.29 (d, J = 6.9 Hz, 1H), 7.59 (d, J = 8.9 Hz, 1H), 7.36 - 7.33 (m, 1H), 6.94 (t, J = 6.7 Hz, 1H), 4.41 (q, J = 7.0 Hz, 2H), 2.70 (s, 3H), 1.42 (t, J = 7.0 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ ppm 161.7, 152.0, 146.1, 127.2, 126.7, 115.9, 112.6, 111.4, 59.5, 16.0, 13.5. MS (ESI) m/z: 205 [M+H]+.

References: [1]Synthesis,2011,p. 635 - 641.
[2]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1947,vol. 67,p. 181.
Chem.Abstr.,1951,p. 9530.
[3]Tetrahedron Letters,2017,vol. 58,p. 3662 - 3666.

2
[ 504-29-0 ]
[ 609-15-4 ]
[ 2549-19-1 ]

Yield	Reaction Conditions	Operation in experiment
62%	In 1,2-dimethoxyethane; at 90℃; for 6h;	4.1.1 Preparation of ethyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate (2) 2-aminopyridine (4.00 g, 42.50 mmol) and 2-chloroethylacetoacetate (7.08 mL, 51.00 mmol) were taken in 1,2-dimethoxyethane (40 mL) and heated at 90 C for 6 h. The reaction mixture was concentrated under reduced pressure, diluted with EtOAc (80 mL), washed the organic layer with H2O (3 * 30 mL). The separated organic layer was dried over anhy Na2SO4 and concentrated under vacuo to get crude compound. The crude compound was purified by column chromatography using 15% EtOAc in hexanes as eluent to get ethyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate (2) (5.40 g, 62%) as an off-white solid. ESI-MS showed 205 [M+H]+ and carried to next step.
46%	In ethanol;Heating / reflux;	Dissolved 2-aminopyridine (2.0 g, 21.2 mmol) in absolute ethanol (100 mL) and added ethyl 2-chloro-3-oxobutanoate (2.7 mL, 19.5 mmol). Refluxed reaction overnight, then concentrated solvent and brought up residue in dichloromethane. Extracted with water twice, followed by a wash with saturated aqueous sodium chloride. Dried over magnesium sulfate and concentrated. Purified by silica gel chromatography on a 0-7% of 2N methanolic ammonia in dichloromethane to afford 2.0 g (46% yield) of ethyl 2- methylimidazo[1 ,2-a]pyridine-3-carboxylate. 1H NMR (400 MHz, DMSO-D6) δ 1.32 (t, <n="75"/>3H), 2.56 (s, 3H), 4.32 (q, 2H), 7.13 (t, 1H), 7.48 (t, 1H), 7.63 (d, 1H), 9.17 (d, 1H); MS m/z 205 (M+1).
	With sodium hydrogencarbonate; In 1,1-dichloroethane; at 22℃;Reflux;	Intermediate 11: 2-[(E)-2-(2-(2,2-Dimethylpropoxy)-3-methoxyphenyl)vinyl]imidazo[1,2-c]pyridine-3-carboxylic acid; Step 1 Ethyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate: To a stirred solution of 2-aminopyridine (15.0 g. 159.00 mmol) in dimethoxyethane (150 mL) was added NaHCO3 (14.72 g, 175 mmol) followed by ethyl 2-chloroacetoacetate (39.34 g, 239 mmol) at room temperature. After refluxing for 16 h the solvent was removed under reduced pressure. The residue was taken up in water (200 mL) and extracted with dichloromethane (2×200 mL). The combined organic layers were washed with water (100 mL), brine (100 mL), and dried over anhydrous Na2SO4. Evaporation of solvents under reduced pressure afforded crude product which was further purified by column chromatography to give 20 g of the product as an off-white solid; 1H NMR (300 MHz, CDCl3) δ 1.44 (t, J=6.9 Hz, 3H), 2.72 (s, 3H), 4.43 (q, J=7.2 Hz, 2H), 6.98 (t, J=6.6 Hz, 1H), 7.38 (t, J=8.7 Hz, 1H), 7.62 (d, J=8.7 Hz, 1H), 9.31 (d, J=6.9 Hz, 1H); ESI-MS (m/z) 205.13 (MH)+.

With sodium hydrogencarbonate; In 1,2-dimethoxyethane; at 20℃;Reflux;

Step 1 Ethyl 2-methylimidazo[l,2-a]pyridine-3-carboxylate: To a stirred solution of 2-aminopyridine (15.0 g. 159.00 retool) in dimethoxyethane (150 mE) was added NaHCO3(14.72 g, 175 retool) followed by ethyl 2-chloroacetoacetate (39.34 g, 239 retool) at roomtemperature. After refluxing for 16 h the solvent was removed under reduced pressure.The residue was taken up in water (200 mL) and extracted with dichloromethane (2 x 200mE). The combined organic layers were washed with water (100 mE), brine (100 mE),and dried over anhydrous NazSO4. Evaporation of solvents under reduced pressureafforded crude product which was further purified by column chromatography to give 20g of the product as an off-white solid; H NMR (300 MHz, CDC13) 8 1.44 (t, J= 6.9 Hz,3H), 2.72 (s, 3H), 4.43 (q, J = 7.2 Hz, 2H), 6.98 (t, J = 6.6 Hz, 1H), 7.38 (t, J = 8.7 Hz,1H), 7.62 (d, J= 8.7 Hz, 1H), 9.31 (d, J= 6.9 Hz, 1H); ESI-MS (m/z) 205.13 (MH)+.

References: [1]European Journal of Medicinal Chemistry,1998,vol. 33,p. 225 - 235.
[2]Il Farmaco,2002,vol. 57,p. 825 - 832.
[3]Journal of Medicinal Chemistry,2012,vol. 55,p. 7525 - 7545.
[4]New Journal of Chemistry,2016,vol. 40,p. 8846 - 8854.
[5]Journal of Medicinal Chemistry,1989,vol. 32,p. 2204 - 2210.
[6]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 4223 - 4232.
[7]Patent: WO2007/87548,2007,A2 .Location in patent: Page/Page column 73-74.
[8]New Journal of Chemistry,2019,vol. 43,p. 16281 - 16299.
[9]Farmaco, Edizione Scientifica,1982,vol. 37,p. 22 - 35.
[10]Patent: US2010/152192,2010,A1 .Location in patent: Page/Page column 14.
[11]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1870 - 1873.
[12]Journal of Medicinal Chemistry,2014,vol. 57,p. 5293 - 5305.
[13]Patent: WO2010/70452,2010,A1 .Location in patent: Page/Page column 32.

3
[ 2549-19-1 ]
[ 21801-79-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With water; lithium hydroxide; In ethanol; at 20℃;	To the stirred solution of <strong>[2549-19-1]ethyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate</strong> (2) (2.00 g) in ethanol/Water (1:1) (30 mL)was added LiOH (4.00 g) and stirred at room temperature for 4 h.The reaction mixture was concentrated to half volume, and added 6N HCl at 0C till the reaction mixture turned to pH 6, the solids formed were filtered and dried in vacuum oven to get 2-methylimidazo[1,2-a]pyridine-3-carboxylic acid (4) (1.53 g, 88%) as an offwhitesolid. ESI-MS showed 177 [M+H]+.

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 7525 - 7545.
[2]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 4223 - 4232.
[3]New Journal of Chemistry,2019,vol. 43,p. 16281 - 16299.
[4]Farmaco, Edizione Scientifica,1982,vol. 37,p. 22 - 35.
[5]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1870 - 1873.
[6]Journal of Medicinal Chemistry,2014,vol. 57,p. 5293 - 5305.

4
[ 2549-19-1 ]
[ 144835-67-6 ]

Yield	Reaction Conditions	Operation in experiment
89%	With hydrazine hydrate; In ethanol; water; for 3h;Reflux;	To the stirred solution of <strong>[2549-19-1]ethyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate</strong> (2) (2.70 g) in Ethanol (30 mL) was added 35% aqueous solution of N2H4.H2O (25 mL) and refluxed for 3 h. The reaction mixture was concentrated to half volume and cooled onice bath, the solids formed were filtered and dried in vacuum oven to get 2-methylimidazo[1,2-a]pyridine-3-carbohydrazide (3)(2.25 g, 89%) as an off-white solid. ESI-MS showed 191 [M+H]+.

References: [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 4223 - 4232.
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 7525 - 7545.
[3]New Journal of Chemistry,2016,vol. 40,p. 8846 - 8854.
[4]Archiv der Pharmazie,1992,vol. 325,p. 623 - 624.
[5]European Journal of Medicinal Chemistry,1998,vol. 33,p. 225 - 235.

5
[ 2549-19-1 ]
[ 30489-44-2 ]

Yield	Reaction Conditions	Operation in experiment
		Under nitrogen atmosphere, to a suspension of aluminum lithium hydride (1.6 g) in THF (100 ml) was added dropwise a solution of <strong>[2549-19-1]ethyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate</strong> (8.56 g) in THF (100 ml) at 0C under nitrogen atmosphere. The mixture was stirred for 1 hour at 0C, water (1.6 ml), 15% aqueous solution of sodium hydroxide (1.6 ml) and water (4.8 ml) were sequentially and slowly added dropwise to the solution, and the mixture was stirred for 2 hours at room temperature. To the reaction solution was added magnesium sulfate, and the precipitates were removed by filtration. The mixture was concentrated under reduced pressure, to give 2-methylimidazo[1,2-a]pyridine-3-methanol (6.45 g) as pale yellow amorphous. A mixture of 2-methylimidazo[1,2-a]pyridine-3-methanol (1 g) and 4-aminothiophenol (0.65 g) in concentrated hydrochloric acid (10 ml) was stirred for 18 hours at room temperature. 8N aqueous solution of sodium hydroxide was added to adjust pH to 10 at 0C and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was separated and purified by column chromatography (ethanol:ethyl acetate 1:4), to give 3-(4-aminophenylthiomethyl)-2-methylimidazo[1,2-a]pyridine (311 mg) as colorless crystals. m.p. 162 to 164C 1H-NMR (200 MHz, CDCl3) δ 2.00 (3H, s), 3.62 to 3.81 (2H, m), 4.15 (2H, s), 6.49 (2H, d, J = 8.5 Hz), 6.79 to 6.87 (1H, m), 6.92 (2H, d, J = 8.5 Hz), 7.13 to 7.22 (1H, m), 7.49 to 7.55 (1H, m), 8.00 to 8.04 (1H, m) IR (KBr) 3335, 3175, 1597, 1495, 1350, 1296, 1254, 829 cm-1 Elemental Analysis for C15H15N3S·0.2H2O Calcd. C, 66.00; H, 5.69; N, 15.39: Found. C, 66.17; H, 5.69; N, 15.11.

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2204 - 2210.
[2]Patent: EP1422228,2004,A1 .Location in patent: Page 195.

6
[ 2549-19-1 ]
[ 30384-93-1 ]

References: [1]Il Farmaco,2002,vol. 57,p. 825 - 832.

7
[ 2549-19-1 ]
[ 501124-61-4 ]

References: [1]Il Farmaco,2002,vol. 57,p. 825 - 832.

8
[ 2549-19-1 ]
[ 501124-58-9 ]

References: [1]Il Farmaco,2002,vol. 57,p. 825 - 832.

9
[ 2549-19-1 ]
[ 501124-60-3 ]

References: [1]Il Farmaco,2002,vol. 57,p. 825 - 832.

10
[ 2549-19-1 ]
(+/-)-2-methyl-3-(piperidin-2-ylmethyl)imidazo[1,2-a]pyridine [ No CAS ]

References: [1]Il Farmaco,2002,vol. 57,p. 825 - 832.

11
[ 2549-19-1 ]
(+/-)-erythro-(2-methylimidazo[1,2-a]pyridin-3-yl)(piperidin-2-yl)methanol [ No CAS ]

References: [1]Il Farmaco,2002,vol. 57,p. 825 - 832.

12
[ 2549-19-1 ]
(+/-)-threo-(2-methylimidazo[1,2-a]pyridin-3-yl)(piperidin-2-yl)methanol [ No CAS ]

References: [1]Il Farmaco,2002,vol. 57,p. 825 - 832.

13
[ 2549-19-1 ]
2-Methyl-imidazo[1,2-a]pyridine-3-carboxylic acid [1-(4-bromo-phenyl)-meth-(Z)-ylidene]-hydrazide [ No CAS ]