Method for producing aniline derivative
A technology for aniline derivatives and production methods, which are applied in the directions of organic chemistry methods, chemical instruments and methods, chemical/physical processes, etc., and can solve problems such as unsuitability for production methods and the like
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Embodiment 1
[0123] [embodiment 1] the synthesis of aniline derivative Cz5
[0124] (1) Synthesis of TBSCZ5
[0125] [chemical 18]
[0126]
[0127] Put DADPA4.78g, TBSCZ-Br47.6g, Pd(dba) in the flask 2 After adding 1.38 g and 16.6 g of sodium tert-butoxide, the inside of the flask was replaced with nitrogen. Next, 240 mL of toluene and 20 mL of a toluene solution of di-tert-butyl(phenyl)phosphine prepared in advance (concentration: 55 g / L) were added, followed by stirring at 90°C. After 2.5 hours, the reaction solution was cooled to room temperature, and 240 mL of ion-exchanged water was mixed to perform a liquid separation treatment. Furthermore, the organic layer was separated and washed with ion-exchanged water and saturated brine, dried over sodium sulfate, and concentrated. The obtained crude product was dissolved in 200 mL of toluene, 3.5 g of Bailu P activated carbon (manufactured by Osaka Gas Chemical Co., Ltd.) was added, and after stirring at room temperature for 2 hours...
Embodiment 2
[0137] [Example 2] Synthesis of Aniline Derivatives 3Cz-TRI3
[0138] (1) Synthesis of 3TBSCz-TRI3
[0139] [chem 21]
[0140]
[0141] Put TRI3 55.1g, TBSCZ-Br95.4g, Pd(dba) in the flask 2 After adding 2.77 g and 32.4 g of sodium tert-butoxide, the inside of the flask was replaced with nitrogen. Next, 550 mL of toluene and 22 mL of a toluene solution of di-tert-butyl(phenyl)phosphine prepared in advance (concentration: 96 g / L) were added, and stirred at 90°C. After 1.5 hours, the reaction solution was cooled to room temperature, and 550 mL of ion-exchanged water was mixed to perform liquid separation treatment. 11.0 g of Bailu P activated carbon (manufactured by Osaka Gas Chemical Co., Ltd.) was added to the obtained organic layer, and after stirring at room temperature for 1 hour, silica gel filtration was performed, and the filter cake was washed with toluene. Concentrate the filtrate to 660g, drop the concentrated solution into a premixed solution of 22.0g of N,N-d...
Embodiment 3
[0147] [Example 3] Synthesis of aniline derivative 3TPA-CZ3
[0148] (1) Synthesis of TBSCZ3
[0149] [chem 23]
[0150]
[0151] DADPA1.99g, TBSCZ-Br7.22g, Pd(dba) were put into the flask 2 After adding 233 mg and 2.69 g of tert-butoxysodium, the inside of the flask was replaced with nitrogen. Next, 100 mL of toluene and 3.7 mL (concentration: 49 g / L) of a toluene solution of di-tert-butyl(phenyl)phosphine prepared in advance were added, followed by stirring at 90°C. After 2 hours, the reaction liquid was cooled to room temperature, 100 mL of ion-exchanged water was mixed, and the mixture was filtered. The obtained filtrate was dissolved in hot toluene, filtered while hot, and the filtrate was stirred at room temperature. After 18 hours, the precipitate was collected by filtration, washed with methanol, and dried to obtain TBSCZ3 (amount: 3.87 g, yield: 51%). Shown below 1 Measurement results of H-NMR.
[0152] 1 H-NMR (500MHz, DMSO-d 6)δ[ppm]: 7.99(d, J=7.6Hz, 2...
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