Methyl 1-(2,4-dichlorobenzyl)-1H-indazole-3-carboxylate synthesis

7synthesis methods

Product Name:Methyl 1-(2,4-dichlorobenzyl)-1H-indazole-3-carboxylate
CAS Number:252025-50-6
Molecular formula:C16H12Cl2N2O2
Molecular Weight:335.1847

94-99-5 Synthesis

94-99-5
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43120-28-1 Synthesis

1H-INDAZOLE-3-CARBOXYLIC ACID METHYL ESTER

43120-28-1
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Methyl 1-(2,4-dichlorobenzyl)-1H-indazole-3-carboxylate

252025-50-6
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Yield:252025-50-6 89%

Reaction Conditions:

with potassium carbonate in acetone at 70;

Steps:

1

Next, a mixture of methyl indazole-3-carboxylate (2.05g, 11.4mmol), 2,4- dichlorobenzyl chloride (3.35mL, 12.54 mml), and K₂CO₃ (7.Og, 50mmol) in acetone (22mL) was refluxed overnight at a temperature of 70 ⁰C. The reaction mixture was cooled to room temperature, filtered, and the residue was washed with acetone. The combined filtrate was concentrated under vacuum (rotovapor). The solid thus obtained was dissolved in CH₂Cl₂ and filtered to remove any undissolved solid. The solution was then concentrated, diluted with hexane and left in the refrigerator overnight. The precipitated solid was then filtered, washed with a mixture of hexane/ethyl acetate (9: 1) to yield the pure product as a white solid. Yield = 3.5g (89%); m.p. = 144°-146 ⁰C; IH NMR (400MHz, CDCl₃) D 8.31 (d, J = 8.8 Hz, IH), 7.39-7.47 (m, 4H), 7.12 (d, J = 8.8 Hz, IH), 6.71 (d, J = 8.8 Hz, IH), 5.81 (s, 2H), 4.11 (s, 3H).

References:

WO2011/5759,2011,A2 Location in patent:Page/Page column 70