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[ CAS No. 1029438-51-4 ]

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Chemical Structure| 1029438-51-4
Chemical Structure| 1029438-51-4
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Product Details of [ 1029438-51-4 ]

CAS No. :1029438-51-4 MDL No. :MFCD14636486
Formula : C12H9BF2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :250.01 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1029438-51-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P260-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1029438-51-4 ]

  • Downstream synthetic route of [ 1029438-51-4 ]

[ 1029438-51-4 ] Synthesis Path-Downstream   1~5

  • 2
  • [ 1029438-51-4 ]
  • ethyl 7-[4-(tert-butoxycarbonyl)piperazin-1-yl]-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-b]pyridine-3-carboxylate [ No CAS ]
  • ethyl 7-[4-(tert-butoxycarbonyl)piperazin-1-yl]-2-[4-(3,5-difluorophenoxy)phenyl]-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-b]pyridine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With pyridine; copper (II) acetate In dichloromethane at 20℃; for 16h; 55.1 ethyl 7-[4-(tert-butoxycarbonyl)piperazin-1-yl]-2-[4-(3,5-difluorophenoxy)phenyl]-4,5,6,7- tetrahydro-2H-pyrazolo[4,3-b]pyridine-3-carboxylate To a solution of pyridine (0.093 mL, 1.14 mmol), [4-(3,5- difluorophenoxy)phenyl]boronic acid (0.286 g, 1.14 mmol, Intermediate X), and ethyl 7-[4- (tert-butoxycarbonyl)piperazin-1-yl]-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-b]pyridine-3- carboxylate (0.217 g, 0.572 mmol, Intermediate V) in dichloromethane (11 mL) was added copper(II) acetate (0.156 g, 0.858 mmol) at ambient temperature. The reaction mixture was stirred for 16 hours under an atmosphere of air. Saturated aqueous NH4Cl was added, and the resulting solution was filtered through diatomaceous earth. The filtrate was extracted with dichloromethane (3x). The combined organic layers were concentrated under reduced pressure, and the crude product was purified by silica gel chromatography (0-100% ethyl acetate in heptanes) to provide the title compound (0.168 g, 50%). MS (ESI) m/z: 583.7 [M+H]+.
50% With pyridine; copper (II) acetate In dichloromethane at 20℃; for 16h; 55.1 ethyl 7-[4-(tert-butoxycarbonyl)piperazin-1-yl]-2-[4-(3,5-difluorophenoxy)phenyl]-4,5,6,7- tetrahydro-2H-pyrazolo[4,3-b]pyridine-3-carboxylate To a solution of pyridine (0.093 mL, 1.14 mmol), [4-(3,5- difluorophenoxy)phenyl]boronic acid (0.286 g, 1.14 mmol, Intermediate X), and ethyl 7-[4- (tert-butoxycarbonyl)piperazin-1-yl]-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-b]pyridine-3- carboxylate (0.217 g, 0.572 mmol, Intermediate V) in dichloromethane (11 mL) was added copper(II) acetate (0.156 g, 0.858 mmol) at ambient temperature. The reaction mixture was stirred for 16 hours under an atmosphere of air. Saturated aqueous NH4Cl was added, and the resulting solution was filtered through diatomaceous earth. The filtrate was extracted with dichloromethane (3x). The combined organic layers were concentrated under reduced pressure, and the crude product was purified by silica gel chromatography (0-100% ethyl acetate in heptanes) to provide the title compound (0.168 g, 50%). MS (ESI) m/z: 583.7 [M+H]+.
  • 3
  • [ 1029438-51-4 ]
  • 7-[4-(tert-butoxycarbonyl)piperazin-1-yl]-2-[4-(3,5-difluorophenoxy)phenyl]-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-b]pyridine-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine; copper (II) acetate / dichloromethane / 16 h / 20 °C 2: lithium hydroxide monohydrate; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 50 °C
  • 4
  • [ 1029438-51-4 ]
  • tert-butyl 4-{3-carbamoyl-2-[4-(3,5-difluorophenoxy)phenyl]-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-b]pyridin-7-yl}piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine; copper (II) acetate / dichloromethane / 16 h / 20 °C 2: lithium hydroxide monohydrate; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 50 °C 3: ammonia hydrochloride; benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 1 h / 20 °C
  • 5
  • [ 1414356-41-4 ]
  • [ 1029438-51-4 ]
YieldReaction ConditionsOperation in experiment
96% With sodium (meta)periodate In tetrahydrofuran; lithium hydroxide monohydrate at 20℃; for 16h; [4-(3,5-difluorophenoxy)phenyl]boronic acid To a solution of 2-[4-(3,5-difluorophenoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2- dioxaborolane (24.6 g, 74.1 mmol) in tetrahydrofuran (80 mL) and water (20 mL) was added sodium periodate (63.4 g, 296 mmol). The cloudy solution was stirred for 16 h at room temperature. The reaction mixture was filtered through a plug of diatomaceous earth and sodium sulfate. The plug was washed with ethyl acetate, and the combined filtrates were concentrated under reduced pressure. The crude product was purified by a silica gel column and eluted with 25% ethyl acetate in hexanes, then 50% ethyl acetate to 1% methanol in dichloromethane to afford the title compound (17.8 g, 96 %). 1H NMR (400 MHz, dimethyl sulfoxide-d6) δ ppm 6.83 - 6.65 (m, 2H).7.04 - 6.95 (m, 1H), 7.07 (d, J = 8.3 Hz, 2H), 7.86 (d, J = 8.3 Hz, 2H).
96% With sodium (meta)periodate In tetrahydrofuran; lithium hydroxide monohydrate at 20℃; for 16h; [4-(3,5-difluorophenoxy)phenyl]boronic acid To a solution of 2-[4-(3,5-difluorophenoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2- dioxaborolane (24.6 g, 74.1 mmol) in tetrahydrofuran (80 mL) and water (20 mL) was added sodium periodate (63.4 g, 296 mmol). The cloudy solution was stirred for 16 h at room temperature. The reaction mixture was filtered through a plug of diatomaceous earth and sodium sulfate. The plug was washed with ethyl acetate, and the combined filtrates were concentrated under reduced pressure. The crude product was purified by a silica gel column and eluted with 25% ethyl acetate in hexanes, then 50% ethyl acetate to 1% methanol in dichloromethane to afford the title compound (17.8 g, 96 %). 1H NMR (400 MHz, dimethyl sulfoxide-d6) δ ppm 6.83 - 6.65 (m, 2H).7.04 - 6.95 (m, 1H), 7.07 (d, J = 8.3 Hz, 2H), 7.86 (d, J = 8.3 Hz, 2H).
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