4-CHLORO-1-ETHYL-6-METHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLIC ACID ETHYL ESTER synthesis
- Product Name:4-CHLORO-1-ETHYL-6-METHYL-1H-PYRAZOLO[3,4-B]PYRIDINE-5-CARBOXYLIC ACID ETHYL ESTER
- CAS Number:41095-07-2
- Molecular formula:C12H14ClN3O2
- Molecular Weight:267.71
Yield:41095-07-2 57.17%
Reaction Conditions:
Stage #1: 5-Amino-1-ethylpyrazole;diethyl 2-(1-ethoxyethylidene)malonate at 120; for 2 h;
Stage #2: with trichlorophosphate at 115;
Steps:
4
A mixture of l-ethyl-lH-pyrazol-5-amine (16 gm, 0.144 moles) (example 2) and 2-(l-ethoxy-ethylidene)-malonic acid diethyl ester (29 gm, 0.12 moles) (example 3) was stirred at 1200C for about 2 hrs. When the reaction was complete on TLC, crude reaction mixture was concentrated in vacuo to remove ethanol, which was formed as byproduct. Crude residue was taken in phosphorous oxychloride (50 ml) and heated at 115 C for about 12-13 hrs. The reaction mixture was poured into ice-cooled water with continuous stirring. Solid which precipitated out was filtered and dried under vacuum to afford title compound as creamy white solid.Yield: 12 gm (57.17%) m/z: (M++l) 268.28
References:
WO2010/46791,2010,A1 Location in patent:Page/Page column 31
![1H-Pyrazolo[3,4-b]pyridine-5-carboxylic acid, 1-ethyl-4-hydroxy-6-methyl-, ethyl ester](/CAS/20210305/GIF/41095-06-1.gif)
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