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Chemical Structure| 2173361-80-1 Chemical Structure| 2173361-80-1
Chemical Structure| 2173361-80-1

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Tau tracer 2 (Pl-2620) is a tracer used for imaging tau protein aggregates, particularly for diagnosing neurodegenerative diseases.

Synonyms: Pl-2620

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

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Product Details of Tau tracer 2

CAS No. :2173361-80-1
Formula : C15H9FN4
M.W : 264.26
SMILES Code : FC1=NC=CC(C2=NC3=C(C=C2)C4=CN=CC=C4N3)=C1
Synonyms :
Pl-2620
English Name :2-(2-Fluoropyridin-4-yl)-9H-pyrrolo[2,3-b:4,5-c']dipyridine
MDL No. :MFCD34179537

Safety of Tau tracer 2

Application In Synthesis of Tau tracer 2

* 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.

  • Downstream synthetic route of [ 2173361-80-1 ]

[ 2173361-80-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1699749-05-7 ]
  • [ 401815-98-3 ]
  • [ 2173361-80-1 ]
YieldReaction ConditionsOperation in experiment
63% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 115℃; for 6h; 1.A To a mixture of degassed 1 ,4-dioxane (4.3 mL) and water (1 mL) in a microwave vial was added [1 ,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(ll), complex with dichloromethane (0.0084 g, 0.01 mmol), followed by the title compound from Preparative Example A (0.05 g, 0.2 mmol), (2-fluoropyridin-4-yl)boronic acid (0.035 g, 0.245 mmol) and cesium carbonate (0.133 g, 0.41 mmol). The reaction mixture was then heated at ~115°C in a sand-bath for 6 hours. The reaction mixture was diluted with ethyl acetate (60 mL) and water (20 mL), the organic phase was separated, dried over Na2S04, filtered and the solvents were evaporated in vacuo. The dark residue was purified by chromatography on silica (25 g HP-SIL) using a Biotage Isolera system employing a dichloromethane/methanol gradient (100/0 -> 95/5 -> 90/10 -> 80/20) to afford the title compound F-3a as an off-white solid (0.033 g, 63 %). (0203) 1H-NMR (400 MHz, DMSO-d6) δ = 12.50 (br-s, 1H), 9.45 (s, 1 H), 8.83 (d, 1 H), 8.56-8.52 (m, 1H), 8.43-8.39 (m, 1 H), 8.19-8.14 (m, 2H), 7.92 (s, 1H), 7.54-7.50 (m, 1 H) (0204) MS (ESI): m/z = 265.04 [M+H]+
63% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 115℃; for 6h; Microwave irradiation; Inert atmosphere; 1.A Example 1 Step A To a mixture of degassed 1 ,4-dioxane (4.3 ml_) and water (1 ml_) in a microwave vial was added [1 ,1 '-bis(diphenylphosphino)ferrocene]dichloropalladium(ll), complex with dichloromethane (0.0084 g, 0.01 mmol), followed by the title compound of Preparative Example A (0.05 g, 0.2 mmol), (2-fluoropyridin-4-yl)boronic acid (0.035 g, 0.245 mmol) and cesium carbonate (0.133 g, 0.41 mmol). The reaction mixture was then heated at ~1 15°C in a sand-bath for 6 hours. The reaction mixture was diluted with ethyl acetate (60 mL) and water (20 mL), the organic phase was separated, dried over Na2S04, filtered and the solvents were evaporated in vacuo. The dark residue was purified by chromatography on silica (25 g HP-SIL) using a Biotage Isolera system employing a dichloromethane/methanol gradient (100/0 -> 95/5 -> 90/10 -> 80/20) to afford the title compound 1 (lb) as an off-white solid (0.033 g, 63 %). (0289) 1H-NMR (400 MHz, DMSO-d6) d = 12.50 (br-s, 1 H), 9.45 (s, 1 H), 8.83 (d, 1 H), 8.56-8.52 (m, 1 H), 8.43-8.39 (m, 1 H), 8.19-8.14 (m, 2H), 7.92 (s, 1 H), 7.54-7.50 (m, 1 H) (0290) MS (ESI): m/z = 265.04 [M+H]+
63% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 115℃; for 6h; 1.A Step A To a mixture of degassed 1 ,4-dioxane (4.3 mL) and water (1 ml_) in a microwave vial was added [1 ,T-bis(diphenylphosphino)ferrocene]dichloropalladium(ll), complex with dichloromethane (0.0084 g, 0.01 mmol), followed by the title compound of Preparative Example A (0.05 g, 0.2 mmol), (2-fluoropyridin-4-yl)boronic acid (0.035 g, 0.245 mmol) and cesium carbonate (0.133 g, 0.41 mmol). The reaction mixture was then heated at ~115°C in a sand-bath for 6 hours. The reaction mixture was diluted with ethyl acetate (60 mL) and water (20 mL), the organic phase was separated, dried over Na2S04, filtered and the solvents were evaporated in vacuo. The dark residue was purified by chromatography on silica (25 g HP-SIL) using a Biotage Isolera system employing a dichloromethane/methanol gradient (100/0 -> 95/5 -> 90/10 -> 80/20) to afford the title compound 1 as an off-white solid (0.033 g, 63 %).1H-NMR (400 MHz, DMSO-d6) d = 12.50 (br-s, 1 H), 9.45 (s, 1 H), 8.83 (d, 1 H), 8.56-8.52 (m, 1 H), 8.43-8.39 (m, 1 H), 8.19-8.14 (m, 2H), 7.92 (s, 1 H), 7.54-7.50 (m, 1 H)MS (ESI): m/z = 265.04 [M+H]+
34% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In N,N-dimethyl acetamide; water at 150℃; for 1h; Inert atmosphere; Microwave irradiation; 5.1.2.1 2-(2-fluoropyridin-4-yl)-9H-pyrrolo[2,3-b:4,5-c']dipyridine (1) In a 5mL microwave tube compound 4 (0.025g, 0.1mmol) and (2-fluoropyridin-4-yl)boronic acid (0.032g, 0.22mmol) were dissolved in DMA (1.4mL). A 2M aqueous sodium carbonate solution (0.224mL, 0.448mmol) was added, and the resulting stirring solution was degassed for 5min. After the addition of Pd(dppf)Cl2×CH2Cl2 (0.0047g, 0.0056mmol), the reaction mixture was heated at 150°C for 1h using a Biotage Initiator microwave. The reaction mixture was diluted with ethyl acetate/MeOH (50mL; 9/1) and a water/brine solution (30mL; 1/1). The organic layer was separated dried with Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica (12g, puriFlash, Interchim) using a Biotage Isolera system employing a CH2Cl2/MeOH gradient (100/0 -> 90/10 -> 80/20 -> 80/20) to afford 1 as a reddish solid (0.0093g, 34%). The analytical data of compound 1 matched the reported data.

  • 2
  • [ 2173361-80-1 ]
  • [ 2173353-59-6 ]
YieldReaction ConditionsOperation in experiment
With rhodium; deuterium 18.A Example 18 (deuterated compound) The title compound from Example 1 was used as starting material to prepare Example 18 ([2H]F-3a) via direct Hydrogen Isotope Exchange with rhodium black. (0330) MS (ESI): m/z = 265 (45%) [M+H]+; 266 (65%) [M+H]+; 267 (100%) [M+H]+; 268 (34%) [M+H]+
 

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