ChemicalBook > CAS DataBase List > 3-ACETYL-2-METHYLIMIDAZO[1,2-A]PYRIDINE

3-ACETYL-2-METHYLIMIDAZO[1,2-A]PYRIDINE

Product Name: 3-ACETYL-2-METHYLIMIDAZO[1,2-A]PYRIDINE
CAS No.: 29096-60-4
Chemical Name: 3-ACETYL-2-METHYLIMIDAZO[1,2-A]PYRIDINE
Synonyms: BUTTPARK 15\05-98;3-ACETYL-2-METHYLIMIDAZO[1,2-A]PYRIDINE;1-(2-methylimidazo[3,2-a]pyridin-3-yl)ethanone;1-(2-methyl-3-imidazo[3,2-a]pyridinyl)ethanone;1-(2-MethyliMidazo[1,2-a]pyridin-3-yl)ethanone;1-(2-METHYLIMIDAZO[1,2-A]PYRIDIN-3-YL)-1-ETHANONE;Ethanone, 1-(2-methylimidazo[1,2-a]pyridin-3-yl)-;1H-Benzimidazole-1-acetonitrile,2,3-dihydro-4-oxo-
CBNumber: CB9149764
Molecular Formula: C10H10N2O
Formula Weight: 174.2
MOL File: 29096-60-4.mol

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3-ACETYL-2-METHYLIMIDAZO[1,2-A]PYRIDINE Property

Melting point:: 112
storage temp.: Sealed in dry,Room Temperature
Appearance: White to off-white Solid

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Safety

Hazard Codes: Xi
Hazard Note: Irritant
HS Code: 2933399990

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

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

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

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N-Bromosuccinimide Price

TRC

Product number: M323855
Product name: 1-(2-Methylimidazo[1,2-a]pyridin-3-yl)ethanone
Packaging: 50mg
Price: $45
Updated: 2021/12/16

TRC

Product number: M323855
Product name: 1-(2-Methylimidazo[1,2-a]pyridin-3-yl)ethanone
Packaging: 100mg
Price: $60
Updated: 2021/12/16

TRC

Product number: M323855
Product name: 1-(2-Methylimidazo[1,2-a]pyridin-3-yl)ethanone
Packaging: 500mg
Price: $130
Updated: 2021/12/16

ChemScene

Product number: CS-W021207
Product name: 1-(2-Methylimidazo[1,2-a]pyridin-3-yl)ethanone
Purity: 99.94%
Packaging: 10g
Price: $650
Updated: 2021/12/16

Matrix Scientific

Product number: 073050
Product name: 3-Acetyl-2-methylimidazo[1,2-a]pyridine
Purity: 95+%
Packaging: 1g
Price: $347
Updated: 2021/12/16

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3-ACETYL-2-METHYLIMIDAZO[1,2-A]PYRIDINE Chemical Properties,Usage,Production

Synthesis

504-29-0

1694-29-7

29096-60-4

Example 1: Synthesis of 3-acetyl-2-methylimidazo[1,2-A]pyridine 1. To a stirred solution of 2-aminopyridine (1.035 g, 11 mmol) in 1,2-dimethoxyethane (5 mL) was added sodium bicarbonate (0.924 g, 11 mmol) and 3-chloro-2,4-pentanedione (2 g, 14.8 mmol). The non-homogeneous reaction mixture was refluxed for about 16 hours and then cooled to room temperature. The volatiles were removed under vacuum. The residue was diluted with water (50 mL) and extracted with dichloromethane (3 x 50 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The crude product was purified by silica gel column chromatography using ethyl acetate/hexane (6:4) as eluent to afford 1-(2-methylimidazo[1,2-a]pyridin-3-yl)ethanone (1 g, yield 38% based on 3-chloro-2,4-pentanedione, 54% based on 2-aminopyridine) as a solid. 2. Bromine (0.163 mL, 3.1 mmol) was added to 1-(2-methylimidazo[1,2-a]pyridin-3-yl)ethanone (500 mg, 2.8 mmol) in 33% hydrobromic acid in acetic acid solution (5 mL, w/v) and stirred at 0°C. The mixture was stirred at room temperature for about 1.5 hours. The reaction mixture was diluted with ether (50 mL) and stirred for about 30 minutes. The resulting solid was filtered and washed with ether (2 x 10 mL) to give 2-bromo-1-(2-methylimidazo[1,2-a]pyridin-3-yl)ethanone (581 mg, 80%) as a solid. 3. To a solution of 2-bromo-1-(2-methylimidazo[1,2-a]pyridin-3-yl)ethanone (2.5 g, 9.88 mmol) in ethanol (25 mL) was added ethyl 3-thioureido-benzoate (2.213 g, 9.88 mmol) and the mixture was refluxed overnight. The ethanol was removed under vacuum and the residue was diluted with ether (75 mL) and stirred for 30 minutes. The solid was filtered and dried under vacuum to give ethyl 3-[4-(2-methylimidazo[1,2-a]pyridin-3-yl)thiazol-2-ylamino]benzoate (2.8 g, 75%) as a solid. 4. To a stirred solution of ethyl 3-[4-(2-methylimidazo[1,2-a]pyridin-3-yl)thiazol-2-ylamino]benzoate (300 mg, 0.79 mmol) in methanol:dichloromethane (15 mL:6 mL) was slowly added 50% aqueous hydroxylamine (6 mL) at 0 °C. After stirring for about 10 minutes at 0°C, a solution of sodium hydroxide (240 mg dissolved in 1.5 mL of water) was added dropwise for about 15 minutes, brought to room temperature and stirred for about 3 hours. The volatiles were evaporated under vacuum below 35°C, diluted with water (6 mL) and cooled to 0°C. The pH was adjusted to about 7 using 2N hydrochloric acid and stirred for about 30 minutes. The resulting solid was filtered, washed with water (75 mL) and dried under vacuum for about 5 h to give 3-acetyl-2-methylimidazo[1,2-A]pyridine (150 mg, 51%) as an off-white solid. MS m/z 366.0 (M++1), melting point 170.4 °C. 1H NMR (DMSO-D6, 200 MHz) δ 2.52 (s, 3H) 7.00 (dd, 1H), 7.10 (s, 1H), 7.2-7.4 (m, 3H), 7.53 (d, 1H), 7.67 (d, 1H), 8.20 (s, 1H), 9.03 (s, OH), 9.05 (d, 1H), 10.54 (s, NH), 11.18 (s, NH).

References

[1] Journal of Medicinal Chemistry, 1989, vol. 32, # 9, p. 2204 - 2210
[2] Patent: US2009/5374, 2009, A1. Location in patent: Page/Page column 140
[3] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 9, p. 2245 - 2248
[4] Journal of the Chilean Chemical Society, 2010, vol. 55, # 4, p. 483 - 485
[5] Patent: EP1214318, 2003, B1. Location in patent: Page/Page column 33

3-ACETYL-2-METHYLIMIDAZO[1,2-A]PYRIDINE Preparation Products And Raw materials

Raw materials

Preparation Products

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3-ACETYL-2-METHYLIMIDAZO[1,2-A]PYRIDINE Suppliers

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29096-60-4, 3-ACETYL-2-METHYLIMIDAZO[1,2-A]PYRIDINERelated Search:

3-Bromoimidazo[1,2-a]pyrimidine 3-BROMO-1H-PYRROLE (5-BROMO-PYRIDIN-3-YL)-METHANOL Methyl 3-oxo-2,3-dihydro-1H-indene-4-carboxylate 3-BroModihydro-2H-pyran-4(3H)-one 3-Acetyl-2-fluoropyridine methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylate ETHYL ISOQUINOLINE-3-CARBOXYLATE ethyl 3-oxo-2,3-dihydro-1H-indene-4-carboxylate 3-Acetyl-2-bromopyridine 3-oxoisoindoline-5-carbonitrile Ethyl 3-bromoisoxazole-5-carboxylate 3-BroMopyrazine-2-carbonitrile 3-Ethylpyrazin-2-amine N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)acetamide 3-BROMO-THIOBENZAMIDE 3-Bromobenzamidine hydrochloride Pyridazine, 3-bromo- (9CI)

BUTTPARK 15\05-98

1-(2-METHYLIMIDAZO[1,2-A]PYRIDIN-3-YL)-1-ETHANONE

3-ACETYL-2-METHYLIMIDAZO[1,2-A]PYRIDINE

1-(2-MethyliMidazo[1,2-a]pyridin-3-yl)ethanone

1-(2-methyl-3-imidazo[3,2-a]pyridinyl)ethanone

1-(2-methylimidazo[3,2-a]pyridin-3-yl)ethanone

Ethanone, 1-(2-methylimidazo[1,2-a]pyridin-3-yl)-

1H-Benzimidazole-1-acetonitrile,2,3-dihydro-4-oxo-

29096-60-4

C10H10N2O

Heterocycle-Pyridine series