8-BENZYLOXY-2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER synthesis
- Product Name:8-BENZYLOXY-2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER
- CAS Number:96428-50-1
- Molecular formula:C18H18N2O3
- Molecular Weight:310.35
24016-03-3
338 suppliers
$5.00/1g
609-15-4
445 suppliers
$6.00/25g
96428-50-1
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$49.00/100mg
Yield:96428-50-1 54%
Reaction Conditions:
in ethanol at 100; for 48 h;Molecular sieve;
Steps:
1A Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate
Example 1A
Ethyl 8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylate
25 g (124.8 mmol) of 2-amino-3-benzyloxypyridine were dissolved in 781 ml of ethanol, 102.7 g (624.2 mmol) of ethyl 2-chloroacetoacetate and two tablespoons of 4 A molecular sieve were added, and the reaction mixture was then heated at reflux (bath temperature 100° C.) for 2 days.
The mixture was concentrated, and excess ethyl 2-chloroacetoacetate was removed on a rotary evaporator with dry ice cooling.
The residue was purified by silica gel chromatography (mobile phase cyclohexane:ethyl acetate gradient 9:1, 4:1).
This gave 20.81 g of the target compound (54% of theory, purity 99%).
LC-MS (Method 2): Rt=1.12 min
MS (ESpos): m/z=311 (M+H)+
1H NMR (400 MHz, DMSO-d6): 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:
US2014/128386,2014,A1 Location in patent:Paragraph 0984; 0985; 0986; 0987; 0988
537-46-2
1 suppliers
$29.50/1mL
24016-03-3
338 suppliers
$5.00/1g
609-15-4
445 suppliers
$6.00/25g
96428-50-1
48 suppliers
$49.00/100mg