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8-Benzyloxy-2-methyl-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester

CAS No.
96428-50-1
Chemical Name:
8-Benzyloxy-2-methyl-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester
Synonyms
2-carboethoxy-3-methyl-8-(phenylmethoxy)imidazo<1,2-a>pyridine;Imidazo[1,2-a]pyridine-3-carboxylicacid, 2-methyl-8-(phenylm...;Ethyl 8-(Benzyloxy)-2-MethyliMidazo[1,2-a]pyridine-3-carboxylate;Ethyl 8-(benzyloxy)-2-MethylH-iMidazo[1,2-a]pyridine-3-carboxylate;ethyl 2-methyl-8-phenylmethoxyimidazo[1,2-a]pyridine-3-carboxylate;8-Benzyloxy-2-methyl-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester;2-Methyl-8-(phenylmethoxy)imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester;Imidazo[1,2-a]pyridine-3-carboxylic acid, 2-methyl-8-(phenylmethoxy)-, ethyl ester
CBNumber:
CB6198736
Molecular Formula:
C18H18N2O3
Molecular Weight:
310.35
MDL Number:
MFCD06739215
MOL File:
96428-50-1.mol
MSDS File:
SDS
Last updated:2026-09-12 18:54:01

8-Benzyloxy-2-methyl-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester Properties

Density 1.18±0.1 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
pka 5.26±0.10(Predicted)

8-Benzyloxy-2-methyl-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester price More Price(27)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Synthonix E59208 Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate 95+% 96428-50-1 100mg $25 2026-05-06 Buy
Synthonix E59208 Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate 95+% 96428-50-1 250mg $60 2026-05-06 Buy
Synthonix E59208 Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate 95+% 96428-50-1 1g $70 2026-05-06 Buy
Synthonix E59208 Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate 95+% 96428-50-1 5g $250 2026-05-06 Buy
Synthonix E59208 Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate 95+% 96428-50-1 10g $1270 2026-05-06 Buy
Product number Packaging Price Buy
E59208 100mg $25 Buy
E59208 250mg $60 Buy
E59208 1g $70 Buy
E59208 5g $250 Buy
E59208 10g $1270 Buy

8-Benzyloxy-2-methyl-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester Chemical Properties, Uses, Production

Synthesis

2-Amino-3-benzyloxypyridine

24016-03-3

Ethyl 2-chloroacetoacetate

609-15-4

8-BENZYLOXY-2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER

96428-50-1

Example 1A Synthesis of ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate: 25 g (124.8 mmol) of 2-amino-3-benzyloxypyridine was dissolved in 781 ml of anhydrous ethanol, followed by the addition of 102.7 g (624.2 mmol) of ethyl 2-chloroacetoacetate and 2 tablespoons of 4A molecular sieves. The reaction mixture was heated to reflux (oil bath temperature 100 °C) for 2 days. Upon completion of the reaction, the mixture was concentrated and excess ethyl 2-chloroacetoacetate was removed by rotary evaporator under dry ice cooling conditions. The residue was purified by silica gel column chromatography with a mobile phase of cyclohexane: ethyl acetate (gradient elution from 9:1 to 4:1). Finally, 20.81 g of the target compound ethyl 2-methyl-8-(benzyloxy)imidazo[1,2-a]pyridine-3-carboxylate was obtained in 54% yield and 99% purity. The product was analyzed by LC-MS (Method 2): retention time Rt = 1.12 min, mass spectrum (ESpos): m/z = 311 (M + H)+. 1H NMR (400 MHz, DMSO-d6) data were as follows: δ= 1.35 (t, 3H), 2.59 (s, 3H), 4.34 (q, 2H), 5.32 (s, 2H). 7.01-7.09 (m, 2H), 7.33-7.48 (m, 3H), 7.52 (d, 2H), 8.81-8.86 (m, 1H).

References

[1] Patent: US2014/128386, 2014, A1. Location in patent: Paragraph 0984; 0985; 0986; 0987; 0988
[2] Patent: US2014/128372, 2014, A1. Location in patent: Paragraph 0489; 0490; 0491; 0492; 0493
[3] Patent: US2017/57954, 2017, A1. Location in patent: Paragraph 0620; 0621; 0622; 0623; 0624
[4] Patent: US2016/347770, 2016, A1. Location in patent: Paragraph 0691; 0692; 0693; 0694; 0695
[5] Journal of Medicinal Chemistry, 1985, vol. 28, # 7, p. 876 - 892

24016-03-3
609-15-4
96428-50-1
Synthesis of 8-Benzyloxy-2-methyl-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester from 2-Amino-3-benzyloxypyridine and Ethyl 2-chloroacetoacetate

8-Benzyloxy-2-methyl-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester Preparation Products And Raw materials

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Ethyl 8-(Benzyloxy)-2-MethyliMidazo[1,2-a]pyridine-3-carboxylate Ethyl 8-(benzyloxy)-2-MethylH-iMidazo[1,2-a]pyridine-3-carboxylate 2-Methyl-8-(phenylmethoxy)imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester ethyl 2-methyl-8-phenylmethoxyimidazo[1,2-a]pyridine-3-carboxylate 2-carboethoxy-3-methyl-8-(phenylmethoxy)imidazo<1,2-a>pyridine Imidazo[1,2-a]pyridine-3-carboxylic acid, 2-methyl-8-(phenylmethoxy)-, ethyl ester Imidazo[1,2-a]pyridine-3-carboxylicacid, 2-methyl-8-(phenylm... 8-Benzyloxy-2-methyl-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester 96428-50-1