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In methanol; dichloromethane; N,N-dimethyl-formamide;
Example 86 6-(2-BROMO-5-METHYL-PHENYL)-N-(4-CHLORO-PHENYL)-[1,3,5]TRIAZINE-2,4-DIAMINE To a suspension of <strong>[6967-82-4]2-bromo-5-methyl-benzoic acid</strong> (3.0 g, 14 mmol) in dichloromethane (100 ml) was added a solution of oxalyl chloride in dichloromethane (2 M, 8 ml, 16 mmol) followed by N,N-dimethylformamide (5 drops). After stirring for 30 minutes, methanol (15 ml) was added. After stirring for 3 hours, the mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate (200 ml) and saturated aqueous potassium carbonate solution (100 ml). The organic layer was concentrated under reduced pressure to provide methyl 2-bromo-5-methyl-benzoate (3.2 g, 99% yield).
methyl 2-((1-benzyl-1H-indol-5-yl)amino)-5-methylbenzoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; at 190℃; for 1.5h;
[Example 205] (1250) (1251) To the solution of 108 mg of 2-bromo-5-methylbenzoic acid in 10 mL of methanol, 0.5 mL of concentrated sulfuric acid was added, and the resultant was heated at reflux for three hours. The reaction mixture was cooled to room temperature, and a saturated aqueous sodium bicarbonate solution and ethyl acetate were then added thereto. The organic layer was separated and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to give methyl 2-bromo-5-methylbenzoate. (1252) To the obtained methyl 2-bromo-5-methylbenzoate, 110 mg of <strong>[26807-73-8]1-benzyl-1H-indol-5-amine</strong>, 10 mg of tris(dibenzylideneacetone)dipalladium(0), 18 mg of 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene, 342 mg of cesium carbonate and 4 mL of toluene were added, and the resultant was stirred at 190C for one hour and 30 minutes using microwave equipment. After cooling the reaction mixture to room temperature, the insoluble matter was filtered off and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (gradient elution with hexane:ethyl acetate = 100:0-75:25) to give methyl 2-((1-benzyl-1H-indol-5-yl)amino)-5-methylbenzoate as a yellow oil. MS (ESI, m/z): 371 (M+H)+.
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