2-PHENYL-PYRAZOLO[1,5-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER synthesis
- Product Name:2-PHENYL-PYRAZOLO[1,5-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER
- CAS Number:51065-76-0
- Molecular formula:C16H14N2O2
- Molecular Weight:266.29
Yield:51065-76-0 65.7%
Reaction Conditions:
with potassium carbonate at 20; for 18 h;
Steps:
38.A A: Preparation of Ethyl 2-phenylpyrazolon,5-a1pyridine-3-carboxylate:
Example 38 l-(2-phenyl-2,4,5,6-tetrahvdrocvclopenta[c]pyrazol-3-yl)-3-(2-phenylpyrazolo[L5-a]pyridin- 3-yl)urea [00673] Step A: Preparation of Ethyl 2-phenylpyrazolon,5-a1pyridine-3-carboxylate: To a solution of 1-aminopyridinium iodide (2.22 g, 10.0 mmol) in DMF (20 mL) was added K2C03 (1.93 g, 14.0 mmol) and ethyl 3-phenylpropiolate (3.30 mL, 20.0 mmol). The mixture was stirred at ambient temperature for 18 hours and was poured into chilled water (100 mL). The mixture was stirred for 30 minutes and was filtered through packed Celite, rinsing with EtOAc and H20. The organic layer was removed and was washed with H20 (4x), dried over MgS04, filtered and concentrated. The residual dark red-orange oil was purified by silica chromatography using a 10-50% EtOAc/hexanes gradient elution to furnish the title compound as a yellow solid (1.75 g, 65.7% yield). MS (apci) m/z = 267.0 (M+H).
References:
WO2014/78408,2014,A1 Location in patent:Paragraph 00673
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