ChemicalBook CAS DataBase List Methyl 5-((4-broMo-2-fluorophenyl)aMino)-4-fluoro-1-Methyl-1H-benzo[d]iMidazole-6-carboxylate

Methyl 5-((4-broMo-2-fluorophenyl)aMino)-4-fluoro-1-Methyl-1H-benzo[d]iMidazole-6-carboxylate synthesis

10synthesis methods

Product Name:Methyl 5-((4-broMo-2-fluorophenyl)aMino)-4-fluoro-1-Methyl-1H-benzo[d]iMidazole-6-carboxylate
CAS Number:1415559-93-1
Molecular formula:C16H12BrF2N3O2
Molecular Weight:396.19

Methyl 5-aMino-4-fluoro-1-Methyl-1H-benzo[d]iMidazole-6-carboxylate

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Methyl 5-((4-broMo-2-fluorophenyl)aMino)-4-fluoro-1-Methyl-1H-benzo[d]iMidazole-6-carboxylate

1415559-93-1
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Yield:1415559-93-1 58.1 %

Reaction Conditions:

with tris-(dibenzylideneacetone)dipalladium⁽⁰⁾;caesium carbonate;Xantphos in 1,2-dimethoxyethane at 90;Inert atmosphere;Sealed tube;

Steps:

2 Step 2: Synthesis of compound 5-((4-bromo-2-fluorophenyl)amino)-4-fluoro-1-methyl-1H-benzimidazole-6-carboxylic acid methyl ester

4-fluoro-5-amino-1-methyl-1H-benzimidazole-6-carboxylic acid methyl ester (200mg, 0.9mmol) and 2-fluoro-4-bromo-1-iodobenzene (300mg, 0.99mmol), Pd2(dba)3 (16mg, 0.017mmol), Xantphos (26mg, 0.044mmol) and cesium carbonate (584mg, 1.79mmol) were added to a 20ml microwave tube, and 8ml of ethylene glycol dimethyl ether was added under nitrogen protection , sealed and heated to 90° C. for 1 hour in microwave, TLC monitored the completion of the reaction, concentrated to remove the solvent after cooling down to room temperature, purified by silica gel column chromatography to obtain 208 mg of yellowish brown solid, yield: 58.1%

References:

WO2022/262699,2022,A1 Location in patent:Page/Page column 32-33