6-BODIPY amide-indoles compound, preparation method and method for detecting living cell multi-nucleation as fluorescent probe
A technology of fluoroborate dipyrrole amide and fluorescent probe, which is applied in the fields of biotechnology and chemistry, and achieves the effects of precise universality, low cost and universality
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Embodiment 1
[0042] Embodiment 1 (making intermediate 1 and 2)
[0043] 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, extracted with EtOAc (200 mL), and 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 obtain the product as a red powder with a yield of 54%.
[0044] 1 H NMR (400MHz, CDCl 3 ): 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 2
[0047] Embodiment 2 (making intermediates 1 and 2)
[0048] 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 28 o C for 4.5 hours. Dry TEA (750 mg, 7.4 mmol) was added and BF was added dropwise after 20 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, extracted with EtOAc (200 mL), and 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 / EtOAC5:1) to give the product as a red powder in 53% yield.
[0049] 1 H NMR (400MHz, CDCl 3 ): δ = 2.30 (s, 3H), 2.36 (s, 3H), 2.59 (s, 3H), 2.62 (s, 3H), 6.23 (s, 1H), 7.13 (s, 1H). HRMS (ES...
Embodiment 3
[0052] Embodiment 3 (making intermediate 1 and 2)
[0053] 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 24 o C for 4.2 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 52 o C, stirred for 2.2 hours. The reaction mixture was evaporated to dryness with a rotary evaporator, extracted with EtOAc (200 mL), and 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 / EtOAC5:1) to give the product as a red powder in 52% yield.
[0054] 1 H NMR (400MHz, CDCl 3): δ = 2.30 (s, 3H), 2.36 (s, 3H), 2.59 (s, 3H), 2.62 (s, 3H), 6.23 (s, 1H), 7.13 (s, 1...
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