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[ CAS No. 1150114-80-9 ]

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Chemical Structure| 1150114-80-9
Chemical Structure| 1150114-80-9
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CAS No. :1150114-80-9 MDL No. :MFCD09870053
Formula : C8H9BN2O2 Boiling Point : 397.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :175.98 g/mol Pubchem ID :44118215
Synonyms :

Safety of [ 1150114-80-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
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Application In Synthesis of [ 1150114-80-9 ]

  • Downstream synthetic route of [ 1150114-80-9 ]

[ 1150114-80-9 ] Synthesis Path-Downstream   1~15

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  • [ 32084-59-6 ]
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  • [ 1327166-33-5 ]
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  • [ 1150114-80-9 ]
  • [ 1367874-63-2 ]
  • [ 1367875-46-4 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate; sodium carbonate;di-tert-butyl[dichloro({di-tert-butyl[4-(dimethylamino)phenyl]phosphaniumyl})palladio][4-(dimethylamino)phenyl]phosphanium; In water; acetonitrile; at 150℃; for 0.666667h;Inert atmosphere; Microwave irradiation; Example 136-( 1 -Methyl- 1 H-indazol-6-yl)-4-(tetrahydro-2H-pyran-4-yloxy)-1H-pyrazolo[4, 3-c]pyridineStep 13-( 1 -Methyl- 1 H-indazol-6-yl)-4-(tetrahydro-2H-pyran-4-yloxy)-1-trityl- 1 H-pyrazolo[4, 3-c]pyridine 3-iodo-4-(tetrahydro-2/-/-pyran-4-yloxy)-1-trityl-1H-pyrazolo[4,3-c]pyridine (100 mg, 0.170 mmol), 1-methyl-1/-/-indazol-6-ylboronic acid (42 mg, 0.238 mmol), bis(di-ferf-butyl(4- dimethylaminophenyI)phosphine) dichloropalladium (12 mg, 0.017 mmol), potassium acetate (23.4 mg, 0.238 mmol) and sodium carbonate (25.2 mg, 0.238 mmol) were charged into a microwave vial equipped with a stir bar. Acetonitrie (1.6 mL) and degassed water (0.6 mL) were then added and the reaction mixture was degassed with nitrogen for 5 min and then heated to 150 C under microwave irradiation for 40 min. The crude mixture was filtered through Celite, and concentrated to give the title compound.
  • 4
  • [ 1268867-67-9 ]
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  • [ 1268864-64-7 ]
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  • [ 1268867-67-9 ]
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  • [ 1396749-96-4 ]
YieldReaction ConditionsOperation in experiment
29% With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 90℃; for 0.333333h;Inert atmosphere; Step 1. Methyl 3-(isopropyl(methyl)amino)-2-(l-methyl-7H-indazol-6-yl)quinoxaline-6- carboxylateTo a solution of methyl 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (Scheme I, 180.0 mg, 0.61 mmol) in dioxane (1 mL) was added l-methyl-iH-indazol-6- ylboronic acid (276.0 mg, 1.57 mmol), K3P04 (391.2 mg, 1.85 mmol), and Pd(PPh3)4 (35.0 mg, 0.03 mmol) under nitrogen atmosphere. After stirring 20 min at 90C, the reaction mixture was dissolved in dichloromethane (30 mL), washed with water (3 x 20 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford a residue, which was purified by a silica gel column with 0.05% - 0.2% ethyl acetate in petroleum ether to afford methyl 3-(isopropyl(methyl)amino)-2-(l-methyl-7H-indazol-6- yl)quinoxaline-6-carboxylate as a light yellow solid (70 mg, 29%).LC/MS (ES, m/z): [M+H]+ 390.0*H-NMR (300 MHz, CDC13) delta 8.55 (d, J = 2.4 Hz, 1H), 7.99 - 8.09 (m, 4H), 7.82 - 7.85 (m, 1H), 7.65 - 7.68 (m, 1H), 4.25 - 4.32 (m, 1H), 4.18 (s, 3H), 4.01 (s, 3H), 2.77 (s, 3H), 1.08 (d, 7 = 6.6 Hz, 6H)
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  • [ 1314883-33-4 ]
  • [ 1416315-08-6 ]
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  • [ 1170193-16-4 ]
  • [ 1150114-80-9 ]
  • [ 1435103-12-0 ]
  • 8
  • [ 1150114-80-9 ]
  • (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate [ No CAS ]
  • [ 1471249-95-2 ]
YieldReaction ConditionsOperation in experiment
Preparation of (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(1-methyl-1H-indazol-6-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetic acid: The reaction mixture of (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (20 mg, 0.039 mmol), <strong>[1150114-80-9]1-methyl-1H-indazole-6-boronic acid</strong> (10.3 mg, 0.058 mmol), 2N K2CO3 (100 muL, 0.19 mmol), Pd(PPh3)4 (4.3 mg, 0.004 mmol) in dioxane (1.5 mL) in sealed tube was heated at 110 C. for 2 h. After the starting material consumed, the reaction was cooled down, to the mixture was added MeOH, excess NaOH, the reaction mixture was heated at 45 C. overnight. Then the reaction mixture was neutralized by acetic acid, concentrated down, then treated by MeOH, and purified by reverse phase HPLC, eluting by 0-100% acetonitrile in H2O with 0.1% TFA to give the product. LCMS-ESI+: calc'd for C33H29ClN4O3S: 597.2 (M+H+). Found: 597.2 (M+H+). 1H NMR (400 MHz, CD3OD): delta 8.78 (d, J=2.6 Hz, 1H), 8.60 (s, 1H), 8.26 (s, 1H), 8.06 (s, 1H), 8.03-7.82 (m, 4H), 7.71-7.69 (m, 1H), 7.61-7.60 (m, 3H), 5.28 (s, 1H), 4.16 (s, 3H), 2.64 (s, 3H), 0.98 (s, 9H).
  • 9
  • 20-acetyl-7-chlorocamptothecin [ No CAS ]
  • [ 1150114-80-9 ]
  • [ 1579279-87-0 ]
YieldReaction ConditionsOperation in experiment
90% With tetrakis(triphenylphosphine) palladium(0); cesium fluoride; In 1,4-dioxane; at 120℃; for 0.5h;Inert atmosphere; Microwave irradiation; General procedure: Compound 7(1eq), 8c (1.5eq), Pd(PPh3)4 (0.1eq) and CsF (2eq) were dissolvedin dioxane (5 mL) in a microwave vial under nitrogen atmosphere and thereaction mixture was irradiated in a microwave apparatus at 120 C for 30 min.After the reaction mixture was cooled to ambient temperature, the crude mixturewas purified by silica gel column chromatography (chloroform: acetone = 30: 1) to afford 9a-g.
  • 10
  • [ 1150114-80-9 ]
  • tert-butyl (2-(((3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)carbamate [ No CAS ]
  • tert-butyl N-[2-(methyl((3-(1-methyl-1H-indazol-6-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)amino)ethyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; at 95℃;Inert atmosphere; A mixture of tert-butyl N-[2-([[3-iodo-1-(oxan-2-yl)-1H-pyrazol-4-yl]methyl](methyl)amino)ethyl]carbamate (200 mg, 0.43 mmol, 1.00 equiv), K3PO4 (273 mg, 1.29 mmol, 3.00 equiv), <strong>[1150114-80-9](1-methyl-1H-indazol-6-yl)boronic acid</strong> (113 mg, 0.64 mmol, 1.50 equiv) and Pd(dppf)Cl2.CH2Cl2 (70 mg, 0.10 mmol, 0.20 equiv) in ethylene glycol dimethyl ether (20 mL) was stirred under nitrogen at 95 C. overnight. The resulting mixture was cooled to room temperature then concentrated under vacuum. The crude product was purified by Pre-HPLC with the following conditions (1-Pre-HPLC-005 (Waters)): Column, XBridge Shield RP18 OBD Column, 5 m, 19×150 mm; mobile phase, water with 10 mmol NH4HCO3 and CH3CN (18% CH3CN up to 58% in 10 min, up to 95% in 1 min, down to 18% in 2 min); Detector, UV 254/220 nm to yield 50 mg (25%) of tert-butyl 2-(methyl((3-(1-methyl-1H-indazol-6-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)amino)ethylcarbamate as a colorless oil. LCMS (method A, ESI): RT=1.16 min, m/z=469.0 [M+H]+.
  • 11
  • [ 1150114-80-9 ]
  • (S)-methyl 1-(3-fluoro-2-methylphenyl)-3-(((trifluoromethyl)sulfonyl)oxy)cyclopent-2-enecarboxylate [ No CAS ]
  • (S)-methyl 1-(3-fluoro-2-methylphenyl)-3-(1-methyl-1H-indazol-6-yl)cyclopent-2-enecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
176 mg With tetrakis(triphenylphosphine) palladium(0); cesium fluoride; In methanol; 1,2-dimethoxyethane; at 120℃; for 2h;Sealed tube; Microwave irradiation; Step 1: (^-methyl l-(3-fluoro-2-methylphenyl)-3-(l-methyl-lH-indazol-6-yl)cyclopent- 2-enecarboxylate [00283] (^-Methyl l-(3-fluoro-2-methylphenyl)-3- (((trifluoromethyl)sulfonyl)oxy)cyclopent-2-enecarboxylate (300 mg, 0.79 mmol), (1- methyl-lH-indazol-6-yl)boronic acid (139 mg, 0.79 mmol), CsF (200 mg), DME (15 mL), MeOH (3 mL) and palladium tetrakis(triphenylphosphine) (20 mg) were combined in a sealed tube and heated by microwave to 120 C for 2 h. The reaction mixture was then evaporated to dryness onto silica and purified by flash chromatography (gradient elution, 0-100% EtOAc in so-hexane) to give the title compound as a colorless gum (176 mg).
  • 12
  • [ 1150114-80-9 ]
  • methyl 3'-fluoro-2'-methyl-4-(((trifluoromethyl)sulfonyl)oxy)-1,2,3,6-tetrahydro-[1,1'-biphenyl]-1-carboxylate [ No CAS ]
  • methyl 3'-fluoro-2'-methyl-4-(1-methyl-1H-indazol-6-yl)-1,2,3,6-tetrahydro-[1,1'-biphenyl]-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,2-dimethoxyethane; at 85℃; for 24h;Inert atmosphere; Sealed tube; Step 1 : methyl 3'-fluoro-2'-methyl-4-(1 -methyl-1 H-indazol-6-yl)-1 , 2,3, 6-tetrahydro- [1 ,1 '-biphenyl]-1 -carboxylate [00379] To a solution of methyl 3'-fluoro-2'-methyl-4- (((trifluoromethyl)sulfonyl)oxy)-1 ,2,3,6-tetrahydro-[1 , 1 '-biphenyl]-1 -carboxylate (600 mg, 1 .51 mmol) in dry DME (8 mL) in a reaction tube was added 1 -methyl- 1 H-indazol-6-yl boronic acid (270 mg, 1 .51 mmol) and Cs2CO3 (1 .48 g, 4.55 mmol). The resulting mixture was degased with nitrogen bubbling for 5 min. Pd(dppf)CI2.CHCI3 (49 mg, 0.061 mmol) was added, the tube sealed and the reaction heated at 85 C for 24 h. The reaction was evaporated to dryness and partioned between water (25 mL) and EtOAc (2 x 25 mL). The organic layers were combined and condensed. The crude product was purified using a Biotage 25 g SNAP column eluting with 0-20% EtOAc in hexane to give the title compound as a colourless oil (500 mg, 88%).
  • 13
  • [ 1150114-80-9 ]
  • methyl 4-((N-(4-bromophenyl)morpholine-4-carboxamido)methyl)benzoate [ No CAS ]
  • methyl 4-((N-(4-(1-methyl-1H-indazol-6-yl)phenyl)morpholine-4-carboxamido)methyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 16h; (Formula 8-6: methyl 4-((N-(4-(1-methyl-1H-indazol-6-yl)phenyl)morpholine-4-carboxamido)methyl)benzoate)[436][437]Compound ofFormula 8-5(methyl 4-((N-(4-bromophenyl)morpholine-4-carboxamido)methyl)benzoate; 0.185 g, 0.427 mmol), 1-methyl-indazol-6-ylboronic acid (0.090 g, 0.512 mmol), and Pd(dppf)Cl2(0.035 g, 0.043 mmol) were dissolved in 1,4-dioxane (3 mL), and then sodium carbonate (0.181 g, 1.71 mmol) dissolved in water (1 mL) was added to the reaction solution and stirred at 80 for 16 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate and saturated sodium hydrogen carbonate aqueous solution and concentrated under reduced pressure, and then the residue was purified and concentrated by column chromatography (silica; ethyl acetate/hexane=30%) to give the desired compound ofFormula 8-6(0.112 g, 71%) in the form of a white solid.
  • 14
  • [ 1150114-80-9 ]
  • methyl 4-(((3-bromophenyl)((4-nitrophenoxy)carbonyl)amino)methyl)benzoate [ No CAS ]
  • methyl 4-(((3-(1-methyl-1H-indazol-6-yl)phenyl)((4-nitrophenoxy)carbonyl)amino)methyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,2-dimethoxyethane; water; at 120℃; for 0.25h;Microwave irradiation; (Formula 3-2:methyl 4-(((3-(1-methyl-1H-indazol-6-yl)phenyl)((4-nitrophenoxy)carbonyl)amino)methyl)benzoate)[282][283]Compound ofFormula 3-1(methyl 4-(((3-bromophenyl)((4-nitrophenoxy)carbonyl)amino)methyl)benzoate; 1.00 g, 2.06 mmol), <strong>[1150114-80-9]1-methyl-1H-indazol-6-ylboronic acid</strong> (0.435 g, 2.47 mmol), Pd(dppf)Cl2(0.168 g, 0.206 mmol), and sodium carbonate (0.693 g, 4.53 mmol) were mixed with dimethoxyethane (5 mL)/H2O (5 mL), heated at 120 for 15 minutes under microwave irradiation, and then the temperature was lowered to room temperature. Water was poured into the reaction mixture, and the organic layer was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution, dehydrated with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified and concentrated by column chromatography (silica; ethyl acetate/hexane=30 %) to give the desired compound ofFormula 3-2(1.03 g, 93%) in the form of a white solid.
  • 15
  • [ 1150114-80-9 ]
  • tert-butyl 4-(4-bromo-2,6-difluorobenzoyl)piperazine-1-carboxylate [ No CAS ]
  • tert-butyl 4-(2,6-difluoro-4-(1-methyl-1H-indazol-6-yl)benzoyl)piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 130℃; for 0.5h;Inert atmosphere; Microwave irradiation; tert-Butyl 4-(4-bromo-2,6-difluorobenzoyl)piperazine-l-carboxylate (383.2mg, 0.946 mmol), 1 -methyl- lH-indazol-6-ylboronic acid (166 mg, 0.946 mmol) and potassium phosphate (1.00 g, 4.73 mmol) were suspended in a nitrogen purged solution of Dioxane (6.0 ml) and Water (1.2 ml). The reaction mixture was further purged with nitrogen for 5 minutes. Palladium Tetrakis (109 mg, 0.095 mmol) was added and the reaction solution was purged with nitrogen for 5 more minutes. The mixture was subjected to microwave irradiation at 130 C for 30 minutes resulting in a yellow biphasic solution. The organic layer (top) was removed, filtered through celite and concentrated in vacuo to afford the crude product as a light red powder. The crude product was subjected to FCC (Biotage SNAP 25; Gradient Eluent: 0 - 20% MeOH in in EtOAc with 0.5% triethylamine over 15 CV). This afforded the title compound (327 mg, 76%) as a light beige powder. LC-MS (ES, m z): 421 [M+H]+
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