ChemicalBook CAS DataBase List Methyl cinnoline-6-carboxylate

Methyl cinnoline-6-carboxylate synthesis

5synthesis methods

Product Name:Methyl cinnoline-6-carboxylate
CAS Number:318276-74-3
Molecular formula:C10H8N2O2
Molecular Weight:188.18

4-Chloro-6-cinnolinecarboxylic acid methyl ester

849805-63-6

318276-74-3

The general procedure for the synthesis of methyl cinnoline-6-carboxylate from methyl 4-chlorocinnoline-6-carboxylate was as follows: to a solution of methyl 4-chlorocinnoline-6-carboxylate (192 mg, 0.863 mmol) in dimethylsulfoxide (30 mL) was added sodium formate (70 mg, 1.04 mmol), tetrakis(triphenylphosphine)palladium(0) (198 mg, 0.702 mmol) and N,N-diisopropylethylamine (0.21 mL, 1.21 mmol). The reaction mixture was stirred at 90 °C for 1.5 hours. After completion of the reaction, it was cooled to room temperature, water was added and extracted with ethyl acetate. The organic layer was washed sequentially with water and brine, dried over anhydrous sodium sulfate and evaporated to remove the solvent. The resulting solid was washed with ether and subsequently purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to afford methyl cinnoline-6-carboxylate (16 mg, 0.089 mmol, 10% yield). The product was characterized by 1H-NMR (CDCl3) with the following chemical shift δ (ppm): 4.03 (3H, s), 7.97 (1H, dd, J = 0.8, 6.0 Hz), 8.42 (1H, J = 0.8, 8.0 Hz), 8.59-8.63 (2H, m), and 9.43 (1H, dd, J = 0.8, 6.0 Hz).

67-56-1 Synthesis

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318276-72-1 Synthesis

318276-72-1
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201230-82-2 Synthesis

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318276-74-3
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Yield:318276-74-3 95.34%

Reaction Conditions:

with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;triethylamine at 60;Sealed tube;

Steps:

Preparation of Acid AE

Into a 30-mL sealed tube, was placed 6-bromocinnoline (600.00 mg, 2.870 mmol, 1.00 equiv), MeOH (12.00 L), Pd(dppf)Cl₂(210.01 mg, 0.287 mmol, 0.10 equiv), TEA (871.30 mg, 8.611 mmol, 3.00 equiv), carbon monoxide (10 atm). The resulting solution was stirred for overnight at 60 degrees C in an oil bath. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with 30 mL of H₂O. The resulting solution was extracted with 3x20 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 600 mg (95.34%) of methyl cinnoline-6- carboxylate as a red solid. LCMS (PH-PUK): [M+H]⁺=189.

References:

WO2021/127166,2021,A1 Location in patent:Paragraph 00135-00136

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318276-74-3
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References