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CAS No. : | 5350-57-2 | MDL No. : | MFCD00007624 |
Formula : | C13H12N2 | Boiling Point : | - |
Linear Structure Formula : | (C6H5)2CHNNH | InChI Key : | QYCSNMDOZNUZIT-UHFFFAOYSA-N |
M.W : | 196.25 | Pubchem ID : | 79304 |
Synonyms : |
|
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P261-P264-P270-P272-P280-P301+P310-P302+P352-P330-P333+P313-P363-P405-P501 | UN#: | 2811 |
Hazard Statements: | H301-H317-H411 | Packing Group: | Ⅲ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With sodium t-butanolate;palladium diacetate; XPhos; In toluene; at 90℃; for 3h; | Synthesis Example 13: Synthesis of Intermediate 13 13.5 g (30 mmol) of Intermediate 6, 7.1 g (36 mmol) of benzophenone hydrazone, 4.3 g (45 mmol) of t-BuONa, 0.13 g (0.6 mmol) of Pd(OAc)2, and 0.29 g (0.6 mmol) of 2-dicyclohexylphosphino-2',4,6'-triisopropylbiphenyl were dissolved in 60 mL of toluene and stirred at 90C for 3 hours. The reaction product was cooled to room temperature. Distilled water was added thereto and the product was extracted twice with 100 mL of diethylether and once with 100 mL of dichloromethane. An organic layer was collected and dried using magnesium sulfate, followed by filtration. The solvent was evaporated, and the residue was separated and purified using silica gel column chromatography to obtain 15.6 g (yield: 92 %) of Intermediate 13. This compound was identified using HR-MS. C41H31N3 calc.: 565.2518; and found: 565.2522. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃; for 5h;Inert atmosphere; | General procedure: In a Schlenk tube under nitrogen atmosphere at room temperature were added BINAP (5.5 mol %), Pd(OAc)2 (5 mol %) and Cs2CO3 (1.4 equiv) and toluene (10 mL per mmol of 1bem). The suspension was heated at 80 C for 10 min and benzophenonehydrazone (2.1 equiv) and the chosen substituted starting material 1b-m (1 equiv) were added. The resulting mixture was heated at100 C for the time depicted in Tables 1 and 2. The mixture was poured in water (20 mL per mmol of 1bem) and CH2Cl2 (20 mL per mmol of 1b-m), filtrated on a short pad of Celite, andextracted with CH2Cl2 (320 mL per mmol of 1bem). The combined organic layers were washed with water (320 mL per mmolof 1bem), dried over MgSO4, filtrated and evaporated. The crude product was eluted on a short pad of silica gel using CH2Cl2 aseluent and evaporated. The crude was introduced in a microwavevial with p-toluenesulfonic acid (2 or 3 equiv see Tables 1 and 2) and solvents (see Tables 1 and 2, 10 mL per mmol of 1b-m). The vial was sealed and the suspension was heated at 100 C for the time depicted in Tables 1 and 2. The resulting mixture was poured in water (20 mL per mmol of 1b-m) and extracted with EtOAc (320 mL per mmol of 1bem). The combined layers were driedon MgSO4, filtrated, evaporated purified by silica gel chromatography. |
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