ETHYL 4-CHLORO-1-METHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLATE synthesis
- Product Name:ETHYL 4-CHLORO-1-METHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLATE
- CAS Number:37801-57-3
- Molecular formula:C10H10ClN3O2
- Molecular Weight:239.66
1192-21-8
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87-13-8
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37801-57-3
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Yield:37801-57-3 54%
Reaction Conditions:
Stage #1: 5-Amino-1-methylpyrazole;diethyl 2-ethoxymethylenemalonate at 110; for 1.5 h;
Stage #2: with trichlorophosphate at 110; for 3.5 h;
Steps:
9 5.1.9. Ethyl 4-chloro-1-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (28)
1-Methyl-1H-pyrazol-5-amine (4.85 g, 49.9 mmol) and diethylethoxymethylenemalonate (10 mL, 50 mmol) were heated at110 C for 1.5 h. The ethanol by-product was removed by evaporationunder reduced pressure. Phosphoryl trichloride (12.1 mL,130 mmol) was added and the mixture was heated at 110 C for3.5 h. The mixture was cooled to room temperature and MeCN(5 mL) was added, and then the solution was further cooled downto 10 C. Water (80 mL) was added slowly maintaining the temperaturebelow 10 C and the suspension was stirred at ambient temperatureovernight. The resultant solid was collected by filtration,washed with minimum amount of water and dried under reducedpressure to afford the title compound (6.7 g, 54%) as a white solid;1H NMR (400 MHz, DMSO-d6) d = 8.96 (s, 1H), 8.40 (s, 1H), 4.38 (q,J = 7.0 Hz, 2H), 4.10 (s, 3H), 1.36 (t, J = 7.0 Hz, 3H); 13C NMR(101 MHz, DMSO-d6) d = 163.6, 151.0, 150.7, 137.8, 132.2, 118.0,115.1, 61.5, 34.2, 14.0. LCMS (Method A, UV, ES): RT = 1.00 min,[M+H]+ = 240, 242, 97% purity. These data were in agreement withthose reported in the literature.
References:
Miah, Afjal H.;Champigny, Aurelie C.;Graves, Rebecca H.;Hodgson, Simon T.;Percy, Jonathan M.;Procopiou, Panayiotis A. [Bioorganic and Medicinal Chemistry,2017,vol. 25,# 20,p. 5327 - 5340]
![DIETHYL 2-([(1-METHYL-1H-PYRAZOL-5-YL)AMINO]METHYLENE)MALONATE](/CAS/GIF/37799-77-2.gif)
37799-77-2
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37801-57-3
47 suppliers
$93.00/50mg
87-13-8
459 suppliers
$5.00/5g
37801-57-3
47 suppliers
$93.00/50mg