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CAS No. : | 138517-66-5 | MDL No. : | MFCD06654768 |
Formula : | C16H16N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NWDYSRZJOLDMRE-CKUJCDMFSA-N |
M.W : | 236.31 | Pubchem ID : | 11499644 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
87% | With Pd(dibenzylideneacetone)2 chloroform adduct; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 110℃; for 12h;Inert atmosphere; | General procedure: Chiral diamine (2.67 mmol), 2-bromo-4-alkylaminopyridine (5.88 mmol), NaOtBu (16 mmol), BINAP (0.11 mmol), and Pd(dba)2.CHCl3 (0.11 mmol) were mixed in 45 mL of toluene (which was distilled under Ar over Na-benzophenone) under an inert atmosphere. The mixture was heated to 110 C for 12 h, brought to rt, and transferred to a separatory funnel. The toluene phase was washed with 50 mL of water, after which the two phases were separated. The remaining water phase was washed with CH2Cl2 and the combined organic phases were concentrated under vacuum. The mixture was purified by flash chromatography; the solvent polarity was gradually changed from pure EtOAc to 20:1 EtOAc:NEt3 with each 100 mL mobile phase portion. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With Pd(dibenzylideneacetone)2 chloroform adduct; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 110℃; for 12h;Inert atmosphere; | General procedure: Chiral diamine (2.67 mmol), 2-bromo-4-alkylaminopyridine (5.88 mmol), NaOtBu (16 mmol), BINAP (0.11 mmol), and Pd(dba)2.CHCl3 (0.11 mmol) were mixed in 45 mL of toluene (which was distilled under Ar over Na-benzophenone) under an inert atmosphere. The mixture was heated to 110 C for 12 h, brought to rt, and transferred to a separatory funnel. The toluene phase was washed with 50 mL of water, after which the two phases were separated. The remaining water phase was washed with CH2Cl2 and the combined organic phases were concentrated under vacuum. The mixture was purified by flash chromatography; the solvent polarity was gradually changed from pure EtOAc to 20:1 EtOAc:NEt3 with each 100 mL mobile phase portion. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In dichloromethane; at 20℃; for 29h;Inert atmosphere; | General procedure: An oven dry flask was charged with compound 6 (879 mg, 2.179 mmol, 1 eq.). The flask was washed under argon. DCM (25 mL) is added to the mixture. Then, (R,R)-1,2-diaminocyclohexane or (S,S)-1,2-trans-antracene diamine ((S,S)-7) (1.03 g, 4.359 mmol, 2 eq.), which are dissolved in 10 mL DCM, were added drop wise using syringe pump over 5 h. The reaction mixture was stirred under argon for a day. A total of 25 milliliters of water was added to the solution. The organic phase was extracted three times with each 10 mL DCM. The solvent was evaporated. The product was isolated by silica gel chromatography (eluent: CH2Cl2/MeOH:5/1). |
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