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[ CAS No. 389621-83-4 ] {[proInfo.proName]}

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Chemical Structure| 389621-83-4
Chemical Structure| 389621-83-4
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Product Details of [ 389621-83-4 ]

CAS No. :389621-83-4 MDL No. :MFCD03411951
Formula : C12H16BNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :PUXUKRSBJVVKMD-UHFFFAOYSA-N
M.W : 233.07 Pubchem ID :2773567
Synonyms :

Safety of [ 389621-83-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 389621-83-4 ]

* 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 [ 389621-83-4 ]

[ 389621-83-4 ] Synthesis Path-Downstream   1~22

YieldReaction ConditionsOperation in experiment
26%
  • 3
  • [ 389621-83-4 ]
  • [ 1010120-55-4 ]
  • C18H19N5O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; An appropriate Ar substituted boronic acid derivative (2eq.) is added to a solution of 2-amino-8-bromo-triazolopyridine (Commercially available, BiofocusDPI) in dioxan/water (5:1). K2CO3 (2 eq.) and PdC^dppf (5%) are added to the mixture. The resulting mixture is heated in a microwave oven at 1400C for 15-45 min or heated in an oil bath at 900C for 4 to 16 h until the reaction goes to completion (monitored by LCMS). Water is added and the mixture is extracted with ethyl acetate. The organic layers are combined, dried over anhyd. MgSO4 and evaporated in vacuo to yield the crude product. The crude product is then purified by flash chromatography to give the corresponding 2-amino-5-Ar-triazolopyridine derivative (2).
  • 4
  • [ 389621-83-4 ]
  • [ 870521-18-9 ]
  • C33H31F3N2O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 170℃; for 0.0833333h; Microwave irradiation;
  • 5
  • [ 389621-83-4 ]
  • [ 1402612-54-7 ]
  • [ 1472640-82-6 ]
YieldReaction ConditionsOperation in experiment
58% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere;
  • 6
  • [ 389621-83-4 ]
  • [ 1476719-53-5 ]
  • [ 1476719-54-6 ]
YieldReaction ConditionsOperation in experiment
12% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere;
  • 7
  • [ 389621-83-4 ]
  • [ 143468-13-7 ]
  • [ 1542067-49-1 ]
YieldReaction ConditionsOperation in experiment
89% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate; In 1,2-dimethoxyethane; water; at 110 - 115℃; for 1h;Inert atmosphere; General procedure: To a degassed 3.5:1 mixture of dimethoxyethane and water (2mL), compound 5 (0.5mmol), the appropriate boronic acid (1mmol), PdCl2(dppf)CH2Cl2 (0.025mmol) and sodium bicarbonate (1.5mmol) were added under nitrogen. The mixture was heated for 1-4h. The layers were separated and the organic phase was evaporated. Purification by flash chromatography gave the desired compounds. Following this procedure compounds 1m-n, 6b-e, 6g-h, 6j, 6l-m, 11, 15 were prepared.
  • 8
  • [ 389621-83-4 ]
  • [ 1542067-15-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate / 1,2-dimethoxyethane; water / 1 h / 110 - 115 °C / Inert atmosphere 2: tetrabutylammomium bromide; sodium hydroxide / toluene / 7 h / 40 °C / Inert atmosphere 3: ammonium carbonate / N,N-dimethyl-formamide / 0.5 h / 60 °C / Inert atmosphere
  • 9
  • [ 389621-83-4 ]
  • 6-[4-(piperidine-1-carbonyl)phenyl]pyrrolo[2,3-b]pyridine-1-carboxylic acid 4-nitrophenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydrogencarbonate / 1,2-dimethoxyethane; water / 1 h / 110 - 115 °C / Inert atmosphere 2: tetrabutylammomium bromide; sodium hydroxide / toluene / 7 h / 40 °C / Inert atmosphere
  • 10
  • [ 389621-83-4 ]
  • [ 1402612-57-0 ]
  • [ 1472640-87-1 ]
YieldReaction ConditionsOperation in experiment
40% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere;
  • 11
  • [ 13534-99-1 ]
  • [ 389621-83-4 ]
  • C17H19N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; bismuth(III) oxide; tetrabutylammomium bromide In water at 110℃; for 5h; Sealed tube;
  • 12
  • [ 626-55-1 ]
  • [ 389621-83-4 ]
  • C17H18N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; bismuth(III) oxide; tetrabutylammomium bromide In water at 110℃; for 4h; Sealed tube;
  • 13
  • [ 389621-83-4 ]
  • N-[4-(2-bromothiazol-4-yl)-3-chlorophenyl]-1,1,1-trifluoro-methanesulfonamide [ No CAS ]
  • N-(3-chloro-4-{2-[4-(piperidine-1-carbonyl)phenyl]-1,3-thiazol-4-yl}phenyl)-1,1,1-trifluoromethanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
207 mg With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 100℃; Inert atmosphere; 16 Example 16. Preparation of Compound No. 67 Example 16. Preparation of Compound No. 67 [0159] N-[4-(2-Bromothiazol-4-yl)-3-chloro-phenyl]-l , 1 , 1 -trifluoro-methanesulfonamide (300 mg, 0.71 mmol, 1 eq.), [4-(piperidine-l-carbonyl)phenyl]boronic acid (233 mg, 1.4 eq.) and sodium carbonate (189 mg, 2.5 eq. in 1 mL water) were charged in 5 mL of DMF in a 25 mL glass bottle and aerated with nitrogen gas for 7 min. After adding Pd(PPh3)4 (82.5 mg, 0.1 mmol) the mixture was further purged for 3 min and was heated to 100 °C overnight. The reaction was monitored by LCMS. The reaction mixture was allowed to cool to RT; water (10 mL) was added and the mixture extracted with EtOAc (3x50 mL). The combined organic layer was washed with water (4x50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product, which was purified by reverse phase HPLC to afford N-(3-chloro-4- {2-[4-(piperidine- 1 -carbonyl)phenyl]-l ,3 -thiazol-4-yl} phenyl)- 1 , 1,1- trifluoromethanesulfonamide (207 mg) as a white solid as the free base. 1H NMR (400 MHz, Chloroform-d) δ (ppm): 7.98 (d, J = 8.5 Hz, 1H), 7.89 (d, J = 7.9 Hz, 2H), 7.82 (s, 1H), 7.36 (d, J = 7.9 Hz, 2H), 7.18 (d, J = 2.2 Hz, 1H), 6.98 (dd, J = 8.5, 2.3 Hz, 1H), 3.78 (s, 2H), 3.37 (s, 2H), 1.72 (s, 4H), 1.55 (s, 2H). LCMS (M+l): 530.1.
207 mg With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 100℃; Inert atmosphere; 16 Preparation of Compound No. 67 N-[4-(2-Bromothiazol-4-yl)-3-chloro-phenyl]-1,1,1-trifluoro-methanesulfonamide (300 mg, 0.71 mmol, 1 eq.), [4-(piperidine-1-carbonyl)phenyl]boronic acid (233 mg, 1.4 eq.) and sodium carbonate (189 mg, 2.5 eq. in 1 mL water) were charged in 5 mL of DMF in a 25 mL glass bottle and aerated with nitrogen gas for 7 min. After adding Pd(PPh3)4 (82.5 mg, 0.1 mmol) the mixture was further purged for 3 min and was heated to 100° C. overnight. The reaction was monitored by LCMS. The reaction mixture was allowed to cool to RT; water (10 mL) was added and the mixture extracted with EtOAc (3*50 mL). The combined organic layer was washed with water (4*50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product, which was purified by reverse phase HPLC to afford N-(3-chloro-4-{2-[4-(piperidine-1-carbonyl)phenyl]-1,3-thiazol-4-yl}phenyl)-1,1,1-trifluoromethanesulfonamide (207 mg) as a white solid as the free base. 1H NMR (400 MHz, Chloroform-d) 8 (ppm): 7.98 (d, J=8.5 Hz, 1H), 7.89 (d, J=7.9 Hz, 2H), 7.82 (s, 1H), 7.36 (d, J=7.9 Hz, 2H), 7.18 (d, J=2.2 Hz, 1H), 6.98 (dd, J=8.5, 2.3 Hz, 1H), 3.78 (s, 2H), 3.37 (s, 2H), 1.72 (s, 4H), 1.55 (s, 2H). LCMS (M+1): 530.1.
207 mg With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 100℃; Inert atmosphere; 15 Preparation of Compound No. 67 N-[4-(2-Bromothiazol-4-yl)-3-chloro-phenyl]-1,1,1-trifluoro-methanesulfonamide (300 mg, 0.71 mmol, 1 eq.), [4-(piperidine-1-carbonyl)phenyl]boronic acid (233 mg, 1.4 eq.) and sodium carbonate (189 mg, 2.5 eq. in 1 mL water) were charged in 5 mL of DMF in a 25 mL glass bottle and aerated with nitrogen gas for 7 min. After adding Pd(PPh3)4 (82.5 mg, 0.1 mmol) the mixture was further purged for 3 min and was heated to 100° C. overnight. The reaction was monitored by LCMS. The reaction mixture was allowed to cool to RT; water (10 mL) was added and the mixture extracted with EtOAc (3*50 mL). The combined organic layer was washed with water (4*50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product, which was purified by reverse phase HPLC to afford N-(3-chloro-4-{2-[4-(piperidine-1-carbonyl)phenyl]-1,3-thiazol-4-yl}phenyl)-1,1,1-trifluoromethanesulfonamide (207 mg) as a white solid as the free base. 1H NMR (400 MHz, Chloroform-d) δ (ppm): 7.98 (d, J=8.5 Hz, 1H), 7.89 (d, J=7.9 Hz, 2H), 7.82 (s, 1H), 7.36 (d, J=7.9 Hz, 2H), 7.18 (d, J=2.2 Hz, 1H), 6.98 (dd, J=8.5, 2.3 Hz, 1H), 3.78 (s, 2H), 3.37 (s, 2H), 1.72 (s, 4H), 1.55 (s, 2H). LCMS (M+1): 530.1.
  • 14
  • [ 389621-83-4 ]
  • C13H8Br2N2O2S [ No CAS ]
  • C26H25N3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane at 80℃;
  • 15
  • [ 389621-83-4 ]
  • C8H6ClN3O [ No CAS ]
  • (4-(5-(5-methyl-1,3,4-oxadiazol-2-yl)pyridin-3-yl)phenyl)(piperidin-1-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With [1,1-bis(di-tert-butylphosphino)ferrocene]palladium(II)dichloride; cesium acetate In N,N-dimethyl-formamide at 90℃; for 15h; Sealed tube;
  • 16
  • [ 389621-83-4 ]
  • methyl 2-((2R, 4R)-2-tert-butyl-4-allyl-5-oxo-1,3-dioxolan-4-yl)acetate [ No CAS ]
  • C25H33NO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With lithium acetate; copper diacetate; palladium diacetate In N,N-dimethyl-formamide at 100℃; Inert atmosphere; regioselective reaction; General procedure for MH-type reaction of phenylboronic acid with methyl2-((2R, 4R)-2-tert-Butyl-4-allyl-5-oxo-1, 3-dioxolan-4-yl) acetate (4) General procedure: A mixture of ester 4 (24 mg, 0.094 mmol, 1 equiv), phenylboronic acid (23.2 mg, 0.11 mmol, 1.2 equiv), copper(II) acetate (34.1 mg, 0.187 mmol, 2 equiv), lithium acetate(28.7 mg, 0.28 mmol, 3 equiv) and palladium(II) acetate (3.2 mg, 0.014 mmol, 15% equiv) in DMF (0.5 ml) was stirred for 1.5h-3h at 100oC. Allowed to cool to room temperature, the reaction mixture was diluted with EtOAc and washed with 1M solution of HCl and brine. The organic layer was evaporated to dryness and the residue was purified by flash chromatography using solvent system of n-hexane: EtOAc.The obtained product was used directly for hydrogenation step.
  • 17
  • [ 389621-83-4 ]
  • C16H22BrClN2O3 [ No CAS ]
  • C28H36ClN3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 80℃; for 16h;
  • 18
  • [ 389621-83-4 ]
  • 1-(5-chloro-2-methoxyphenyl)adamantane [ No CAS ]
  • (3'-(adamantan-1-yl)-4'-methoxy[1,1'-biphenyl]-4-yl)(piperidin-1-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With palladium 10% on activated carbon; diisopropylamine In tetrahydrofuran; water at 80℃; for 4h; Sealed tube; General Procedure for the preparation of biaryls General procedure: Toa solution of 1-(5-chloro-2-methoxyphenyl)adamantane (1) (0.3 mmol) in 4:1ratio of THF/H2O taken in a sealed tube was added boronic acid(2a-m) (0.32mmol), diisopropyl amine (0.7mmol), and 10%Pd/C (4 mol%). The reaction mixture was heated to 80 deg for therequired hours .The reaction was then cooled to room temperature and filteredto remove the base and catalyst. The product was extracted by 3×5 mL ethylacetate, dried with magnesium sulfate, filtered, and concentrated in vacuum.The crude product was purified by column chromatography using ethyl acetate:hexane. All new compounds exhibited spectral properties consistent with theassigned structures and were fully characterized by their spectroscopic data (1H,Mass, elemental and 13C NMR analysis).
  • 19
  • [ 389621-83-4 ]
  • bromo-indole [ No CAS ]
  • (4-Methylpiperazin-1-yl)(5-nitro-3-(4-(piperidine-1-carbonyl)phenyl)-1H-indol-2-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine)palladium (0) III (4-Methylpiperazin-1-yl)(5-nitro-3-(4-(piperidine-1-carbonyl)phenyl)-1H-indol-2-yl)methanone (19) (4-Methylpiperazin-1-yl)(5-nitro-3-(4-(piperidine-1-carbonyl)phenyl)-1H-indol-2-yl)methanone (19) Bromoindole 20 (10.0 mg, 0.0272 mmol, 1.0 equiv.), (4-(piperidine-1-carbonyl)phenyl)boronic acid (16.3 mg, 0.0699 mmol, 2.6 equiv.), lithium chloride (˜10 mg) and tetrakis(triphenylphosphine)palladium(0) (3 mg, 10 mol %) were dissolved in 1:1:1 2M sodium bicarbonate:toluene:ethanol (1 mL) and heated at 80° C. for 24 h in a tightly-capped vial under N2. After cooling to room temperature, the reaction mixture was diluted with saturated sodium bicarbonate (5 mL), extracted with CH2Cl2 (3*5 mL). The combined organic layers were dried over Na2SO4 then concentrated under reduced pressure. Purification of the crude by prep. TLC (10% MeOH/CH2Cl2) provided the title compound as a yellow solid (4.1 mg, 32%): 1H NMR (400 MHz, CDCl3) δ 9.65 (s, 1H), 8.70 (s, 1H), 8.22 (d, J=9.2 Hz, 1H), 7.60-7.48 (m, 5H), 3.75 (bs, 4H), 3.47 (bs, 2H), 3.15 (bs, 2H), 2.35 (bs, 3H), 2.14 (s, 2H), 1.67 (m, 8H); HRMS (ESI-TOF+) m/z calc'd for C26H30N5O4 [M+H]+: 476.2292. found 476.2292.
  • 20
  • [ 389621-83-4 ]
  • [ 76-09-5 ]
  • piperidin-1-yl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexyl)methanone [ No CAS ]
  • piperidin-1-yl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diethyl ether / 18 h / 20 °C / Inert atmosphere 2: hydrogen; [Rh(cod)(CI)(CAACMe2)] / 2,2,2-trifluoroethanol / 24 h / 40 °C / 45004.5 Torr / Autoclave; Molecular sieve
  • 21
  • [ 389621-83-4 ]
  • [ 76-09-5 ]
  • [ 938043-31-3 ]
YieldReaction ConditionsOperation in experiment
In diethyl ether at 20℃; for 18h; Inert atmosphere;
  • 22
  • [ 389621-83-4 ]
  • [ 2065-37-4 ]
  • 2-(4-(piperidin-1-ylcarbonyl)phenyl)-1,4-naphthoquinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In tetrahydrofuran; water at 65℃; for 3h; Inert atmosphere; 4.3. General synthetic procedures for arylnaphthoquinones 3a-r General procedure: Under exclusion of air or humidity, bromonaphthoquinone 2(237 mg, 1 mmol) and Cs2CO3 (489 mg, 1.5 mmol) were addedsuccessively to a stirred solution of Pd(PPh3)4 (29 mg, 0.025 mmol)in anhydrous THF (4 mL). Then, 0.6 mL of H2O and 1.5 mmol of thecorresponding boronic acid were added and the reaction mixturewas heated to 65 C until TLC showed complete consumption of thestarting material (1.5e20 h). After cooling to ambient temperature,the mixture was diluted with water (15 mL) and extracted severaltimes with EtOAc. The combined organic layers were dried overNa2SO4 and concentrated in vacuo to give a residue, which waspurified by flash chromatography.
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