Chiral 3-amino-4-arylpyridine nitrogen-oxygen catalyst and application thereof in tetrazole hemiacetal amine ester reaction
A technology of arylpyridine nitrogen oxide catalyst and aryl pyridine nitrogen oxide, which is applied in the synthesis of chiral 3-amino-4-arylpyridine nitrogen oxide catalyst to catalyze the synthesis of tetrazole hemiaminal ester, a new type In the field of chiral DMAP catalysts, it achieves the effects of strong adjustability, simple synthesis and good yield
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[0033] Example 1 Chiral 4-Phenyl-3- (2- (2,6 diisophenylphenylene) pyrrolidinyl) pyridine oxide synthesis
[0034]
[0035] Under nitrogen protection, in a 25 ml seal tube, a chiral 3-pyrrolidin-4-chloropyridine nitrogen oxide (125 mg, 0.31 mmol), phenyl boric acid (152 mg, 1.24 mmol), potassium carbonate (171 mg, 1.24 mmol) ), PD (PPH 3 ) 4 (17.90 mg, 0.015 mmol), XANT-PHOS (14.4 mg, 0.031 mmol) and 2.5 mL of toluene were placed in a 120 ° C oil bath, and the stirring was stopped after 40min. Through TLC monitoring, the rough product was concentrated in vacuo, and then a light brown solid was separated by column chromatography. In this example, the original azogeneous 3-pyrrolidinyl-4-chloropyridine oxide can be synthesized by Angew.Chem. Int.ED.2019, 58, 2839. 1 H NMR (400MHz, CDCL 3 Δ8.35 (S, 1H), 8.08 (S, 1H), 7.85 (D, J = 6.4 Hz, 1H), 7.46-7.34 (M, 5H), 7.26 (T, J = 7.2 Hz, 1H), 7.12 (D, J = 7.6Hz, 2H), 7.04 (D, J = 6.4 Hz, 1H), 4.27 (T, J = 7.2Hz, 1H), 3.24 (DD, J = 16.0, ...
Example Embodiment
[0036] Example 2 Chiral 4-Phenyl-3- (2- (3,5-Difluoromethylphenylene) pyrrolidinyl) pyridine oxide
[0037]
[0038] Under nitrogen, in 25mL sealed tube, were added the chiral 3-pyrrolidinyl-4-chloropyridine N-oxide (125mg, 0.27mmol), benzene boronic acid (134mg, 1.10mmol), potassium carbonate (1.10 mmol), PD (PPH) 3 ) 4 (15.59 mg, 0.0135 mmol), XANT-PHOS (17.4 mg, 0.027 mmol) and 2.5 mL of toluene were placed in a 120 ° C oil bath, and the stirring was stopped after 40min. Through TLC monitoring, the rough product was concentrated in vacuo, and then a light brown solid was separated by column chromatography. In this example, the original azogeneous 3-pyrrolidinyl-4-chloropyridine oxide can be synthesized by Angew.Chem. Int.ED.2019, 58, 2839. 1 H NMR (400MHz, CDCL 3 Δ10.98 (S, 1H), 8.64 (S, 1H), 7.85 (D, J = 6.4 Hz, 1H), 7.61-7.47 (M, 6H), 7.46-7.41 (m, 1H), 7.31 (S 1H), 7.18 (D, J = 6.4 Hz, 1H), 4.57 (T, J = 7.2 Hz, 1H), 3.24-3.10 (m, 1H), 2.81-2.70 (m, 1H), 2.50-2.36 ( M, 1H),...
Example Embodiment
[0039] Example 3 Chiral 4- (3,5-dimethylphenyl) -3- (2- (2,6 diisophenylphenylene) pyrrolidinyl) pyridine oxide
[0040]
[0041] Under a nitrogen protection, a chiral 3-pyrrolidin-4-chloropyridine nitrogen oxide (125 mg, 0.31 mmol), 3,5-dimethyla boric acid (186 mg, 1.24 mmol) was sequentially added. Potassium carbonate (171mg, 1.24 mmol), PD (PPH 3 ) 4 (17.90 mg, 0.015 mmol), XANT-PHOS (14.44 mg, 0.031 mmol) and 2.5 ml of toluene were placed in a 120 ° C oil bath, and the stirring was stopped after 40min. Through TLC monitoring, the rough product was concentrated in vacuo, and then a light brown solid was separated by column chromatography. 1 H NMR (400MHz, CDCL 3 Δ8.20 (S, 1H), 7.83 (DD, J = 6.4, 1.6 Hz, 1H), 7.72 (S, 1H), 7.23 (D, J = 8.0 Hz, 1H), 7.11 (D, J = 8.0 Hz, 2H), 7.02 (D, J = 6.8 Hz, 1H), 6.98 (S, 1H), 6.95 (S, 2H), 4.20 (T, J = 7.2 Hz, 1H), 3.25 (DT, J = 9.6 , 7.6Hz, 1H), 2.93-2.75 (m, 3H), 2.27 (S, 6H), 2.14-2.04 (m, 1H), 1.94-1.81 (m, 1h), 1.13 (D, J = 6.8 Hz, 6...
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