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With sodium t-butanolate; In hexane; ethyl acetate; toluene;
Synthesis of N-(3-(1,3-dioxolan-2-yl)phenyl)dibenzo[b,d]thiophen-4-amine A clean and dry 1000 ml round bottom flask equipped with a reflux condenser, magnetic stir bar, and thermometer with adapter was prepared and purged with nitrogen. A solution of 4-bromodibenzo[b,d]thiophene (RS-1-170, 10.7 g, 0.0407 mol) in anhydrous toluene (500.0 ml) was then prepared and transferred to the reaction flask via cannula. <strong>[6398-87-4]3-aminobenzaldehyde ethylene acetal</strong> (8.1 g, 0.0488 mol) was added by syringe. The reaction solution was purged with a strong nitrogen flow for 20 minutes. Sodium tert-butoxide (5.86 g, 0.0610 mol) and Pd2dba3 (1.10 g, 0.0012 mol) were then added manually, followed by the addition of tri-tert-butylphosphine (0.65 g, 0.0032 mol) in toluene (-10 ml) via syringe. The vessel was heated to reflux for approximately 2 hours. The reaction was then cooled to room temperature and filtered through a Celite and silica gel pad. Solvent was removed by rotary evaporation. The crude material was dissolved in a 2:1 hexane/ethyl acetate solution purified by flash column chromatography using a gradient elution system of ethyl acetate/hexane. This provided pure product confirmed by NMR.
N-(4-chloro-3-methylphenyl)-N-dibenzo[b,d]thiophene-4-amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
53%
With tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate; In toluene; at 100℃; for 10h;Inert atmosphere; Schlenk technique; Sealed tube;
4-bromo showing an argon atmosphere to a stirred 150mL shrink tube having cut by the formula (1-190) 4-bromo-modify benzothiophene 5.79g (22.0mmol), the formula (1-191) represents a 3-chloro methylaniline 3.74g (26.4mmol), potassium -tert- butoxide 3.70g (33.0mmol), acetic acid palladium (II) 99mg (0.44mmol), into a dehydrated toluene 60mL, was degassed.Then, the tree pin -tert- butylphosphine was added to 267mg (1.32mmol) and sealed, and stirred for 10 hours at 100. After cooling to room temperature, adding the reaction mixture into water, followed by extraction with methylene chloride, it was subjected to washing with water.The organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated.Resulting crude () product of hexane: dichloromethane (4: 1) was purified by a silica gel column with eluent chromatography. As doing the above steps, to obtain a compound represented by the formula (1-192) as a quantity 3.75g, yield 53percent.Identification of the compounds was carried out by the molecular ion peak of the object by matching the mass analysis.
53%
With tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate; In toluene; at 100℃; for 10h;Schlenk technique; Inert atmosphere;
In a 150 mL Schlenk tube equipped with a stirring bar, 5.79 g (22.0 mmol) of 4-bromodibenzothiophene represented by the above chemical formula (99), 4-chloro-3- 3.74 g (26.4 mmol) of methylaniline, 3.70 g (33.0 mmol) of potassium-tert-butoxide, 99 mg (0.44 mmol) of palladium (II) acetate and 60 mL of dehydrated toluene were placed and degassed and then tri- Butyl phosphine (267 mg, 1.32 mmol), and the mixture was sealed and stirred at 100 ° C. for 10 hours.After cooling to room temperature, the reaction mixture was poured into water, extracted with methylene chloride, and washed with water. After drying the organic layer with anhydrous sodium sulfate, the solvent was distilled off. The obtained crude product was purified by silica gel column chromatography using hexane: methylene chloride (4: 1) as an eluent.By carrying out the above steps, a compound represented by the above chemical formula (109) was obtained in a yield of 3.75 g in a yield of 53percent. Identification of the compound was carried out by mass spectrometry where the molecular ion peak matched with the object.
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