4-BODIPY amide-indoles compound, preparation method and method for detecting living cell multi-nucleation as fluorescent probe
A technology for fluoroboron dipyrrole amide and compound, which is applied in the fields of biotechnology and chemistry, and achieves the effects of low cost, simple operation and universality
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Embodiment 1
[0043] Embodiment 1 (making intermediate 1 and 2)
[0044] Step (a): 3, 5-dimethylpyrrole-2-carbaldehyde (100mg, 0.81mmol) and 2, 4-dimethylpyrrole-3-cyanide (89mg, 0.74mmol) were dissolved in anhydrous DCM ( 15mL), at 0 o Stir for 10 minutes under argon protection, slowly add POCl 3 (124 mg, 0.81 mmol). response at 0 o C after 1 hour, at 25 o C for 4 hours. Dry TEA (750 mg, 7.4 mmol) was added and BF was added dropwise after 15 minutes 3 ·Et 2 O (0.93ml, 7.4mmol). The reaction mixture was heated to 50 o C, stirred for 2 hours. The reaction mixture was evaporated to dryness with a rotary evaporator and extracted with EtOAc (ethyl acetate) (200 mL), then washed with H 2 O (3×50 mL) washed with Na 2 SO 4 dry. The crude product was purified by silica gel column chromatography (petroleum ether / EtOAC 5:1) to give the product as a red powder in 54% yield. 1 H NMR (400MHz, CDCl 3 Chloroform): δ =2.30 (s, 3H), 2.36 (s, 3H), 2.59 (s, 3H), 2.62 (s, 3H), 6.23 (s, 1H), 7....
Embodiment 2
[0046] Embodiment 2 (making intermediates 1 and 2)
[0047] Step (a): 3, 5-dimethylpyrrole-2-carbaldehyde (100mg, 0.81mmol) and 2, 4-dimethylpyrrole-3-cyanide (89mg, 0.74mmol) were dissolved in anhydrous DCM ( 15mL), at 0 o Stir under argon for 15 minutes, slowly add POCl 3 (124 mg, 0.81 mmol). response at 0 o C after 1.5 hours, at 23 o C for 5 hours. Dry TEA (750 mg, 7.4 mmol) was added, and BF was added dropwise after 18 minutes 3 ·Et 2 O (0.93ml, 7.4mmol). The reaction mixture was heated to 53 o C, stirred for 2.5 hours. The reaction mixture was evaporated to dryness with a rotary evaporator and extracted with EtOAc (ethyl acetate) (200 mL), then washed with H 2 O (3×50 mL) washed with Na 2 SO 4 dry. The crude product was purified by silica gel column chromatography (petroleum ether / EtOAC 5:1) to give the product as a red powder in 54% yield. 1 H NMR (400MHz, CDCl 3 Chloroform): δ =2.30 (s, 3H), 2.36 (s, 3H), 2.59 (s, 3H), 2.62 (s, 3H), 6.23 (s, 1H), 7.13(s...
Embodiment 3
[0049] Embodiment 3 (making intermediate 1 and 2)
[0050] Step (a): 3, 5-dimethylpyrrole-2-carbaldehyde (100mg, 0.81mmol) and 2, 4-dimethylpyrrole-3-cyanide (89mg, 0.74mmol) were dissolved in anhydrous DCM ( 15mL), at 0 o Stir under argon for 9 minutes, slowly add POCl 3 (124 mg, 0.81 mmol). response at 0 o C after 1.2 hours, at 23 o C for 4.5 hours. Dry TEA (750 mg, 7.4 mmol) was added, followed by the dropwise addition of BF after 14 minutes 3 ·Et 2 O (0.93ml, 7.4mmol). The reaction mixture was heated to 51 o C, stirred for 2.2 hours. The reaction mixture was evaporated to dryness with a rotary evaporator and extracted with EtOAc (ethyl acetate) (200 mL), then washed with H 2 O (3×50 mL) washed with Na 2 SO 4 dry. The crude product was purified by silica gel column chromatography (petroleum ether / EtOAC 5:1) to give the product as a red powder in 54% yield. 1 H NMR (400MHz, CDCl 3Chloroform):δ = 2.30 (s, 3H), 2.36 (s, 3H), 2.59 (s, 3H), 2.62 (s, 3H), 6.23 (s...
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