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[ CAS No. 933986-97-1 ]

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Chemical Structure| 933986-97-1
Chemical Structure| 933986-97-1
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CAS No. :933986-97-1 MDL No. :MFCD06798273
Formula : C15H23BN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :274.17 g/mol Pubchem ID :-
Synonyms :

Safety of [ 933986-97-1 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P301+P310 UN#:2811
Hazard Statements:H301 Packing Group:
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Application In Synthesis of [ 933986-97-1 ]

  • Downstream synthetic route of [ 933986-97-1 ]

[ 933986-97-1 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 1015242-14-4 ]
  • [ 933986-97-1 ]
  • 4-(3-cyano-5-(6'-(pyrrolidin-1-yl)-[2,3']bipyridinyl-4-yl)-1H-pyrrol-2-yl)-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In propan-1-ol; water at 145℃; for 0.25h; Irradiation; 102.a a) 4-[3-Cyano-5-(6'-pyrrolidin-1 -yl-[2,3']bipyridinyl-4-yl)-1 H-pyrrol-2-yl]-piperazine-1-carboxylic acid tert-butyl ester. 2-Pyrrolidin-1-yl-5-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-pyridine (425 mg) and 300 mg of 4-[5-(2-chloro-pyridin-4-yl)-3-cyano-1 H-pyrrol-2-yl]-piperazine-1-carboxylic acid tert- butyl ester are dissolved in 8 ml n-propanol. The solution is degassed by introduction of a stream of argon. Pd(PPh2J2CI2 (55 mg) and 1 ml of 2 N Na2CO3 are added and the mixture is heated for 15 min at 145 0C in a microwave oven . The reaction mixture is extracted with ethyl acetate / water/ brine and died over sodium sulfate. After evaporation of the solvent the residue is purified by reverse phase HPLC ( acetonitrile/water ) and yields a yellow solid. 1H-NMR (400 MHz, DMSO-d6): 1.43 (s, 9H), 1.97 (m, 4H),3.38-3.45 (m, 12H>, 6.54 (d, 1 H), 7.13 (d, 1H), 7.39 (dd, 1H), 8.02 (s, 1H), 8.18 (dd, 1H), 8.43 (d, 1H), 8.87 (d, 1H),11.16 (s, 1H). MS (ESI+) m/z: 500 [ MH]+.
  • 3
  • [ 933986-97-1 ]
  • [ 353-83-3 ]
  • [ 1393479-19-0 ]
YieldReaction ConditionsOperation in experiment
57% With tris-(dibenzylideneacetone)dipalladium(0); water; cesium fluoride; copper(l) chloride; XPhos In N,N-dimethyl-formamide at 65℃; for 16h; Inert atmosphere;
  • 4
  • [ 933986-97-1 ]
  • C18H18Cl3FN4O2 [ No CAS ]
  • C27H29Cl2FN6O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene at 80℃; for 8h; 12.3 3) 12c of the . 223 mg (0.5 mM) and 12b of 165 mg (0.6 mM) were dissolved in the mixture (6:1) of ethanol and toluene. The Pd (PPh3)4 of 25 mg and 2M Na2CO3solution of 1 ml were added in the solution. 80 heated the obtained mixture for 8 hours. The reaction mixture was attenuated to the CH2Cl2and it dried using the MgSO4and it filtered and it concentrated and it refined to the gel chromatography. It is manufactured: 12d of 28% (78 mg).
  • 5
  • [ 624-28-2 ]
  • [ 933986-97-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 1.5 h / 110 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.2: 2 h / 20 °C
  • 6
  • [ 61676-62-8 ]
  • [ 210963-93-2 ]
  • [ 933986-97-1 ]
YieldReaction ConditionsOperation in experiment
30% Stage #1: 5-bromo-2-(pyrrolidin-1-yl)pyridine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at 20℃; for 2h; 12.2 2) 12a of 0.52 g (2.3 mM) among THF of the . 15 ml was cooled at -78 and 1.6 M solution of the n-butyl lithium was dipped among the hexane of 1.7 ml. The reaction mixture was stirred for 30 minutes and thereafter 2- isopropoxy -4,4,5,5- tetramethyl -1,3,2- dioxaborolanes (511 mg, 2.7 mM) were added. In the room temperature the mixture, it stationed for 2 hours. Reaction was let be quenched with the aqueous solution of the NaHCO3. The mixture was extracted in the ethyl acetate and it dried using the Na2SO4and the solvent was removed. The obtained boronate can be used as the form which is not refined for the following reaction. It is manufactured: 12b of 190 mg (30%).
  • 7
  • [ 933986-97-1 ]
  • 5-(2,6-dichloro-3-fluorobenzyl)-3-(6-(pyrrolidin-1-yl)pyridin-3-yl)-5,6,7,8-tetrahydropyrazino[2,3-c]pyridazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol / 8 h / 80 °C 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / pH 9
  • 8
  • [ 933986-97-1 ]
  • 3-iodo-1-(1,2,3,4-tetrahydronaphthalen-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine [ No CAS ]
  • 3-(6-(pyrrolidin-1-yl)pyridin-3-yl)-1-(1,2,3,4-tetrahydronaphthalen-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 80℃; for 16h; Inert atmosphere; Synthesis of 3-(6-(pyrrolidin-1-yl)pyridin-3-yl)-1-(1,2,3,4-tetrahydronaphthalen-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (15) Step 1: To a stirred solution of V (0.2 g, 0.51 mmol, 1 eq) and XXXIV (0.20 g, 0.76 mmol, 1.5eq) in 1,4- dioxane (15 mL) was added 2M Na2CO3 (0.13 g, 1.27 mmol, 2.5 eq) and Pd(PPh3)4(0.047 g, 0.040 mmol, 0.08 eq). The resultant mixture was purged with nitrogen gas for 15 minand and stirred at 80 °C for 16 h. Reaction progress was checked using LCMS and TLC. Aftercompletion of reaction, the reaction mixture was diluted with ice cold water (10 mL).Precipitates obtained were filtered over Buchner funnel and re-dissolved using CH2Cl2 andslurry was prepared using SiO2 (100-200 mesh). Purification was carried out using SiO2chromatography (0-4% MeOH in CH2Cl2) to afford the desired product 15 (0.040 g, 19%).
  • 9
  • [ 933986-97-1 ]
  • [ 4175-77-3 ]
  • 4-bromo-2-(6-(pyrrolidin-1-yl)pyridin-3-yl)thiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 1h; Inert atmosphere; A71.1 Step 1 : 4-bromo-2-(6-(pyrrolidin- 1 -yl)pyridin-3-yl)thiazole A mixture of 2,4-dibromothiazole (486 mg, 2.0 mmol, 1.0 eq.), 2-(pyrrolidin-l-yl)-5- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (603 mg, 2.2 mmol, 1.1 eq.), potassium carbonate (828 mg, 6.0 mmol, 3.0 eq.), and PdCh(dppf) (146 mg, 0.2 mmol, 0.1 eq.) in dioxane/water (10 ml 75 mL) was heated at 100 °C for 1 hour under nitrogen protection. The mixture was cooled to room temperature, poured into water, and extracted with ethyl acetate for three times. The organic extracts were combined, washed with brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column using hexane - EtOAc (0-100%)) to give 4-bromo-2-(6-(pyrrolidin-l-yl)pyridin-3-yl)thiazole (520 mg, 84% yield). LC-MS m/z [M+H]+ calc’d for Ci2Hi2BrN3S, 311; found, 311.
  • 10
  • [ 933986-97-1 ]
  • 3-fluoro-2-hydroxy-5-(2-(6-(pyrrolidin-1-yl)pyridin-3-yl)thiazol-4-yl)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 2.1: sodium carbonate / water; 1,4-dioxane / 0.03 h / Inert atmosphere 2.2: 8 h / 105 °C / Sealed tube
  • 11
  • [ 933986-97-1 ]
  • 5-chloro-7-(1-{2-methyl-1-[6-(trifluoromethyl)pyridin-3-yl]propyl}-1H-pyrazol-4-yl)[1,2,4]triazolo[1,5-a]pyridin-2-amine [ No CAS ]
  • 7-(1-{2-methyl-1-[6-(trifluoromethyl)pyridin-3-yl]propyl}-1H-pyrazol-4-yl)-5-[6-(pyrrolidin-1-yl)pyridin-3-yl][1,2,4]triazolo[1,5-a]pyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% With chloro(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1’-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) 2nd generation; sodium carbonate In 1,4-dioxane; water at 90℃; for 3h; Inert atmosphere; II-79 General Procedure A: General procedure: A mixture of the halogenide, the boronic ester and sodium carbonate (or caesium carbonate where stated) was suspended under argon in a mixture of dioxane and water. The mixture was degassed and purged with argon several times. Then the catalyst was added, and the reaction mixture was stirred for 2.5 h at 90 °C. Unless stated otherwise, the reaction mixture was fdtered and the solid washed with ethyl acetate. The fdtrate was evaporated and the residue was suspended in a minimum of dichloromethane. A solid precipitated, which was fdtered off through kieselgur and discarded. The fdtrate was concentrated in vacuo and the residue was further purified.
  • 12
  • [ 933986-97-1 ]
  • 5-(2,3-dihydro-1H-inden-4-yl)-3-iodo-6-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridine [ No CAS ]
  • [ 76-05-1 ]
  • 5-(2,3-dihydro-1H-inden-4-yl)-6-methoxy-3-(6-(pyrrolidin-1-yl)pyridin-3-yl)-1H-pyrazolo[4,3-b]pyridine trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-(pyrrolidin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine; 5-(2,3-dihydro-1H-inden-4-yl)-3-iodo-6-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridine With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; Stage #2: With trifluoroacetic acid In 1,4-dioxane; water at 20℃; for 0.166667h; Inert atmosphere; Stage #3: trifluoroacetic acid 57 Example 57. Example 57. 5-(2,3-Dihydro-1H-inden-4-yl)-6-methoxy-3-(6-(pyrrolidin-1-yl)pyridin-3-yl)-1H-pyrazolo[4,3-b]pyridine To a solution of 5-(2,3-dihydro-1H-inden-4-yl)-3-iodo-6-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridine (Example 53, step 3; 20 mg, 0.04 mmol) in 1,4-dioxane (0.5 mL) and water (0.1 mL) was added 2-(pyrrolidin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (13 mg, 0.047 mmol), potassium phosphate (17 mg, 0.078 mmol), and [dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (3 mg, 4 μmol). The reaction was degassed with N2 and stirred at 80° C. After 2 h, triflic acid (0.5 mL) was added to the reaction mixture at r.t. After 10 min, the reaction mixture was diluted with MeOH and purified by prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min). The product was isolated as the TFA salt. LC-MS calculated for C25H26N5O (M+H)+: m/z=412.2; found 412.2.
  • 13
  • [ 933986-97-1 ]
  • (S)-3-(7-chloro-6-((tetrahydrofuran-3-yl)oxy)imidazo[1,2-b]pyridazin-3-yl)-5-(difluoromethyl)-4-fluoro-N-methylbenzamide [ No CAS ]
  • (S)-3-(difluoromethyl)-4-fluoro-N-methyl-5-(7-(6-(pyrrolidin-1-yl)pyridin-3-yl)-6-((tetrahydrofuran-3-yl)oxy)imidazo[1,2-b]pyridazin-3-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium carbonate In water; N,N-dimethyl-formamide at 110℃; for 0.5h; 32 Example 32 (S)-3-(Difluoromethyl)-4-fluoro-N-methyl-5-(7-(6-(pyrrolidin-1-yl)pyridin-3-yl)-6-((tetrahydrofuran-3-yl)oxy)imidazo[1,2-b]pyridazin-3-yl)benzamide A sample of (S)-3-(7-chloro-6-((tetrahydrofuran-3-yl)oxy)imidazo[1,2-b]pyridazin-3-yl)-5-(difluoromethyl)-4-fluoro-N-methylbenzamide (15 mg, 0.034 mmol, see Example 26, Step 1) was dissolved in DMF (0.4 ml) and water (0.08 ml). This solution was treated with 2-(pyrrolidin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (28 mg, 0.10 mmol) and K2CO3 (14 mg, 0.10 mmol). Pd XPhos G2 (4 mg, 5 μmop was added, the vial was capped, and the solution was stirred at 110° C. After 30 mins, LCMS indicated consumption of the starting material. The solution was cooled to room temperature, diluted with MeCN and water, filtered through a SiliaPrep Thiol cartridge, and purified by HPLC (pH=2 method) to provide (S)-3-(difluoromethyl)-4-fluoro-N-methyl-5-(7-(6-(pyrrolidin-1-yl)pyridin-3-yl)-6-((tetrahydrofuran-3-yl)oxy)imidazo[1,2-b]pyridazin-3-yl)benzamide (2.5 mg, 4.5 μmol, 13% yield). LCMS calculated for C28H28F3N6O3(M+H)+: m/z=553.2; found: 552.9.
  • 14
  • [ 4175-78-4 ]
  • [ 933986-97-1 ]
  • 5-bromo-2-(6-(pyrrolidin-1-yl)pyridin-3-yl)thiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With tripotassium phosphate tribasic; (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1’-biphenyl)[2-(2’-amino-1,1’-biphenyl)]palladium(II) methanesulfonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 140℃; for 1h; Inert atmosphere; Microwave irradiation; 27.1 Example 27: 5-hydroxy-2-(2-(6-(pyrrolidin-1-yl)pyridin-3-yl)thiazol-5-yl)isonicotinaldehyde (Compound 129) Step 1: Synthesis of 5-bromo-2-(6-(pyrrolidin-1-yl)pyridin-3-yl)thiazole: 5-bromo-2- (4-(pyrrolidin-1-yl)phenyl)thiazole, was accomplished by adding 2-(pyrrolidin-1-yl)-5-(3,3,4,4- tetramethylborolan-1-yl)pyridine (150 mg, 0.55 mmol), 2,5-dibromothiazole (199 mg, 0.82 mmol), G3-Pd Xantphos (25.9 mg, 0.03 mmol) and Xantphos (15.8 mg, 0.03 mmol) to a microwave vial. Dioxane (2.7 mL) and degassed 0.5M K3PO4 (2.7 mL) were added and the vial was degassed with argon. The sealed reaction vessel was heated to 140°C in a microwave reactor for 1 hour. The mixture was cooled, diluted with dichloromethane (DCM) and extracted with saturated aqueous NaHCO3. The combined aqueous layers were extracted 2 times more with DCM. The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified using 0-70% DCM/ Hexanes to provide 5-bromo-2-(6- (pyrrolidin-1-yl)pyridin-3-yl)thiazole (69mg, 41% yield). MS m/z [M+H]+ calc’d for C12H12BrN3S, 310; found, 310.
41% With tripotassium phosphate tribasic; (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1’-biphenyl)[2-(2’-amino-1,1’-biphenyl)]palladium(II) methanesulfonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 140℃; for 1h; Inert atmosphere; Microwave irradiation; 27.1 Example 27: 5-hydroxy-2-(2-(6-(pyrrolidin-1-yl)pyridin-3-yl)thiazol-5-yl)isonicotinaldehyde (Compound 129) Step 1: Synthesis of 5-bromo-2-(6-(pyrrolidin-1-yl)pyridin-3-yl)thiazole: 5-bromo-2- (4-(pyrrolidin-1-yl)phenyl)thiazole, was accomplished by adding 2-(pyrrolidin-1-yl)-5-(3,3,4,4- tetramethylborolan-1-yl)pyridine (150 mg, 0.55 mmol), 2,5-dibromothiazole (199 mg, 0.82 mmol), G3-Pd Xantphos (25.9 mg, 0.03 mmol) and Xantphos (15.8 mg, 0.03 mmol) to a microwave vial. Dioxane (2.7 mL) and degassed 0.5M K3PO4 (2.7 mL) were added and the vial was degassed with argon. The sealed reaction vessel was heated to 140°C in a microwave reactor for 1 hour. The mixture was cooled, diluted with dichloromethane (DCM) and extracted with saturated aqueous NaHCO3. The combined aqueous layers were extracted 2 times more with DCM. The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified using 0-70% DCM/ Hexanes to provide 5-bromo-2-(6- (pyrrolidin-1-yl)pyridin-3-yl)thiazole (69mg, 41% yield). MS m/z [M+H]+ calc’d for C12H12BrN3S, 310; found, 310.
  • 15
  • [ 73183-34-3 ]
  • [ 210963-93-2 ]
  • [ 933986-97-1 ]
YieldReaction ConditionsOperation in experiment
100% With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In 1,4-dioxane at 110℃; for 3h; Inert atmosphere; 28.1 Example 28: 3-fluoro-2-hydroxy-5-(3-(6-(pyrrolidin-1-yl)pyridin-3-yl)-1,2,4-thiadiazol-5- yl)benzaldehyde (Compound 130) Step 1: Synthesis of 2-(pyrrolidin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)pyridine: 5-Bromo-2-(pyrrolidin-1-yl)pyridine (2 g, 8.8 mmol, 1.0 eq.) was dissolved in dioxane (30 mL). 4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi(1,3,2-dioxaborolane) (3.37 g, 13.2 mmol, 1.5 eq.), potassium acetate (2.6 g, 26.4 mmol, 3.0 eq.), and PdCl2(dppf) (430 mg, 0.5 mmol, 0.06 eq.) were added. The reaction was heated at 110°C for 3 hours under N2 atmosphere. The solvent was removed in vacuo. The residue as suspended in water and extracted with ethyl acetate for three times. The organic extracts were combined, washed with brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/EtOAc=10:1 to 1:1) to give 2-(pyrrolidin-1-yl)-5-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (2.7 g, quantitative yield) as a yellow oil. LC-MS m/z [M+H]+ calc’d for C15H23BN2O2, 275; found, 275.
100% With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In 1,4-dioxane at 110℃; for 3h; Inert atmosphere; 28.1 Example 28: 3-fluoro-2-hydroxy-5-(3-(6-(pyrrolidin-1-yl)pyridin-3-yl)-1,2,4-thiadiazol-5- yl)benzaldehyde (Compound 130) Step 1: Synthesis of 2-(pyrrolidin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)pyridine: 5-Bromo-2-(pyrrolidin-1-yl)pyridine (2 g, 8.8 mmol, 1.0 eq.) was dissolved in dioxane (30 mL). 4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi(1,3,2-dioxaborolane) (3.37 g, 13.2 mmol, 1.5 eq.), potassium acetate (2.6 g, 26.4 mmol, 3.0 eq.), and PdCl2(dppf) (430 mg, 0.5 mmol, 0.06 eq.) were added. The reaction was heated at 110°C for 3 hours under N2 atmosphere. The solvent was removed in vacuo. The residue as suspended in water and extracted with ethyl acetate for three times. The organic extracts were combined, washed with brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/EtOAc=10:1 to 1:1) to give 2-(pyrrolidin-1-yl)-5-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (2.7 g, quantitative yield) as a yellow oil. LC-MS m/z [M+H]+ calc’d for C15H23BN2O2, 275; found, 275.
  • 16
  • [ 933986-97-1 ]
  • 2-(4-(pyrrolidin-1-yl)phenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1’-biphenyl)[2-(2’-amino-1,1’-biphenyl)]palladium(II) methanesulfonate; tripotassium phosphate tribasic; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 1 h / 140 °C / Inert atmosphere; Microwave irradiation 2: anhydrous potassium acetate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / 1,4-dioxane / 0.75 h / 140 °C / Microwave irradiation
  • 17
  • [ 933986-97-1 ]
  • 5-hydroxy-2-(2-(6-(pyrrolidin-1-yl)pyridin-3-yl)thiazol-5-yl)isonicotinaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1’-biphenyl)[2-(2’-amino-1,1’-biphenyl)]palladium(II) methanesulfonate; tripotassium phosphate tribasic; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 1 h / 140 °C / Inert atmosphere; Microwave irradiation 2: anhydrous potassium acetate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / 1,4-dioxane / 0.75 h / 140 °C / Microwave irradiation 3: dicyclohexyl(2’,4’,6’-triisopropyl-[ 1,1’-bi-phenyl]-2-yl)phosphane; tripotassium phosphate tribasic; methanesulfonato (2-di-tert-butylphosphino-3,4,5,6-tetramethyl-2’,4’,6’-triisopropyl-1,1-biphenyl)(2’-amino-1,1‘-biphenyl-2-yl) palladium(II) / 1,4-dioxane / 0.5 h / 130 °C / Microwave irradiation; Inert atmosphere
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N,N-Diethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

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Chemical Structure| 1257554-16-7

[ 1257554-16-7 ]

N-Ethyl-N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

Similarity: 0.95

Esters

Chemical Structure| 1073354-41-2

[ 1073354-41-2 ]

2-(Pyrrolidin-1-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.96

Chemical Structure| 1225066-77-2

[ 1225066-77-2 ]

(R)-1-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)pyrrolidin-3-ol

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Chemical Structure| 852228-08-1

[ 852228-08-1 ]

2-(Piperidin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.96

Chemical Structure| 1311165-58-8

[ 1311165-58-8 ]

N,N-Diethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

Similarity: 0.96

Chemical Structure| 1251948-86-3

[ 1251948-86-3 ]

1-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperidin-4-ol

Similarity: 0.95

Related Parent Nucleus of
[ 933986-97-1 ]

Pyrrolidines

Chemical Structure| 1073354-41-2

[ 1073354-41-2 ]

2-(Pyrrolidin-1-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.96

Chemical Structure| 1353880-12-2

[ 1353880-12-2 ]

N-(2-(Pyrrolidin-1-yl)propyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

Similarity: 0.94

Pyridines

Chemical Structure| 1073354-41-2

[ 1073354-41-2 ]

2-(Pyrrolidin-1-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.96

Chemical Structure| 852228-08-1

[ 852228-08-1 ]

2-(Piperidin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.96

Chemical Structure| 1311165-58-8

[ 1311165-58-8 ]

N,N-Diethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

Similarity: 0.96

Chemical Structure| 1251948-86-3

[ 1251948-86-3 ]

1-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperidin-4-ol

Similarity: 0.95

Chemical Structure| 1257554-16-7

[ 1257554-16-7 ]

N-Ethyl-N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

Similarity: 0.95