Home Cart 0 Sign in  

[ CAS No. 1073354-96-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1073354-96-7
Chemical Structure| 1073354-96-7
Structure of 1073354-96-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 1073354-96-7 ]

Related Doc. of [ 1073354-96-7 ]

Alternatived Products of [ 1073354-96-7 ]

Product Details of [ 1073354-96-7 ]

CAS No. :1073354-96-7 MDL No. :MFCD09260487
Formula : C11H16BClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :OTPWQANCPKJXBK-UHFFFAOYSA-N
M.W : 254.52 Pubchem ID :43811066
Synonyms :

Safety of [ 1073354-96-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P312 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1073354-96-7 ]

* 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 [ 1073354-96-7 ]

[ 1073354-96-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 588729-99-1 ]
  • [ 73183-34-3 ]
  • [ 1073354-96-7 ]
YieldReaction ConditionsOperation in experiment
43% With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; at 80℃;Inert atmosphere; [0423] To a solution of 5-bromo-2-chloropyridin-3-amine (2.07 g, 10 mmol) in DME (50 mL) were added bis(pinacolato)diboron (3.05 g, 12 mmol), Pd(dppf)Cl2 CH2Cl2 (245 mg, 0.3 mmol), and potassium acetate (2.94 g, 30 mmol). The mixture was stirred overnight at 80 0C under Ar and then allowed to cool to room temperature. Ethyl acetate (200 mL) and water (100 mL) were added to the mixture. Insoluble materials were removed by filtration. Two phases were separated and the aqueous phase was extracted with ethyl acetate (100 mL). The organic extracts were combined and washed with brine (100 mL) and dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated in vacuo. The crude product was purified by silica gel column chromatography eluted with a 10%- 40% mixture of ethyl acetate and hexane. After concentration of appropriate fractions, the residual solid was collected by filtration and washed with hexane to yield titled compound 2-Chloro-5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)pyridin-3-amine (43F, 1.11 g, 43%) as white crystalline solid. 1H NMR (300 MHz, CDCl3): delta 8.13 (d, 1 H, J = 1.6 Hz), 7.40 (d, 1 H, J = 1.6 Hz), 4.02 (br s, 2 H), 1.34 (s, 12 H). MS (ES) [M+H] calc'd for CHH16BCIN2O2, 255; found 255.
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 90℃; for 4h; Step 1. 2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine To a 100 mL, round-bottomed flask was added 5-bromo-2-chloropyridin-3-amine (2 g, 10 mmol, Asymchem Laboratories, Morrisville, N.C.), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (2 g, 10 mmol, Aldrich, St. Louis, Mo.), potassium acetate (0.9 g, 10 mmol), 1,1'-bis(diphenylphosphino)ferrocene-palladium dichloride (7 g, 10 mmol, Strem Chemical, Inc., Newburyport, Mass.), and dioxane (20 mL). The mixture was degassed by Ar for 1 minute, then stirred under N2 protection at 90 C. for 4 h. The black suspension was filtered through a celite pad, the filtercake was washed with MeOH-DCM (50%). The filtrate was concentrated in vacuum. The resulted residue was treated with ether and filtered again. The filtrate was concentrated in vacuo. Purification by silica gel chromatography (20 to 50% (10% MeOH/CH2Cl2)-hexane) and later by recrystallized from methanol-hexane provided 2-chloro-5-(4,4,5-trimethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine as a white solid. MS (ESI positive ion) m/z: 173 and 208 (M+1). 1H NMR (400 MHz, DMSO-d6): delta ppm 1.29 (s, 12H), 5.58 (s, 2H), 7.40 (d, J=1.76 Hz, 1H), 7.76 (d, J=1.76 Hz, 1H).
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 100℃; for 4h;Inert atmosphere; 5-Bromo-2-chloropyridin-3-amine (500 mg, 2.410 mmol), bis(pinacolato)diboron (672.9 mg, 2.649 mmol) and potassium acetate (467 mg, 4.765 mmol) in 1 ,4-dioxane (15 mL) were degassed with argon gas for 15 mm. PdCI2(dppf)dichloromethane complex (98 mg, 0.120 mmol) was added and the reaction mixture was stirred at 100 Cfor4 h. The reaction mixture was diluted with ethyl acetate, filtered through celite and the filtrate was concentrated to afford 800 mg (crude) of 2-chloro-5-(4, 4,5, 5-tetramethyl- 1,3,2- dioxaborolan-2-yI)pyridin-3-amine 98-1 as a deep brown solid. The crude product was used as such for the next step without further purification. ESI-LC/MS: m/z254.9 (M+H) & 256.9 [(M+H)+2]; R = 3.14 mm [Agilent [C with Ion trap Detector; Xterra MS-Cl 8, 2.5 pm, 4.6 X 50 mm column; gradient of 80:20 H20 (0.01 M ammonium bicarbonate):CH3CN to 10:90 H20 (0.01 M ammonium bicarbonate):CH3CN in 4.0 mm and hold for 3.0 mm with flow rate of 1.0 mL/min].
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 80℃; for 2.5h; A stirred mixture of <strong>[588729-99-1]3-amino-5-bromo-2-chloropyridine</strong> (0.151 g), potassium acetate (0.215 g), bis(pinacolato)diboron (0.196 g) and dry 1,4-dioxan was purged with nitrogen for 10 minutes . [1,1 -Bis(diphenylphosphino)ferrocene] dichloropalladium(II) 1 : 1 complex with methylene chloride (0.036 g) was added and the reaction mixture was stirred and heated to 80C for 2.5 hours under nitrogen. 6-Bromo-5-methyl-3-(2-trimethylsilylethoxymethyl)- 3H-imidazo[4,5-]pyridine (0.2 g), 2N aqueous sodium carbonate solution (1.83 ml) and ethanol (0.8 ml) were added in turn and the resultant mixture was purged with nitrogen for 10 minutes. [1,1 -Bis(diphenylphosphino)ferrocene]dichloropalladium(II) l:lcomplex with methylene chloride (0.018 g) was added and the reaction mixture was stirred and heated to 80C for 8 hours. The reaction mixture was partitioned between ethyl acetate and water. The <n="89"/>organic solution was washed with water and with brine, dried over anhydrous sodium sulphate and evaporated. The material so obtained was purified by column chromatography on silica using a gradient from 99:1 to 9:1 of methylene chloride and methanol as eluent. There was thus obtained 6-(5 -amino--chloropyridin-S -yl)-5-methyl-3 -(2-trimethylsilylemoxymethyl)- 3/f-imidazo[4,5-£]pyridine (0.145 g); 1H NMR Spectrum: (DMSOd6) 0.0 (s, 9H), 0.93 (m, 2H), 2.56 (s, 3H + DMSO peak), 3.7 (t, IH), 5.7 (s, 4H), 7.22 (s, IH), 7.68 (s, IH), 7.98 (s, IH), 8.6 (s, IH); Mass Spectrum: M+H* 390 and 392.
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 110℃; for 0.333333h;Inert atmosphere; microwave irradiation; EXAMPLE 32; N-(2-chloro-5-(4-(4-morpholinyl)-6-quinolinyl)-3-pyridinyl)-2- fluorobenzenesulfonamide; (l)2-chloro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin-3- amine.; (Some starting materials may be obtained from Aldrich, St. Louis, MO) To a 5 ml microwave tube was added 5-bromo-2-chloropyridin-3-amine (0.1 g, 0.5 mmol), bis(pinacolato)diboron (0.2 g, 0.7 mmol), potassium acetate (0.2 g, 2 mmol), 1,1'- bis(diphenylphosphino)ferrocene]dichloride palladium(ii) (0.03 g, 0.04 mmol), and dioxane (3 mL). The vial was sealed and placed in Biotage Initiator microwave (Biotage, Charlottesville,VA) for 20 min at 110 0C. LC/MS showed no sign of starting material. Dioxane was removed in vacuo. The residue was partitioned between EtOAc/water. The organic layer was washed with water, brine, dried over MgSO4 and removed solvent. The crude product was purified using SiO2 <n="99"/>(12g) chromatography with hexanes:acetone=85%: 15% as the solvent system to afford the desired product as light yellow solid (75 mg). A peak at 38 min was collected. The solvent was concentrated to afford the desired product as light yellow solid (75 mg). MS (ESI pos. ion) m/z: calc'd for CHH16BCIN2O2: 254.1; found: 255.3 (M+l). 1H NMR (300 MHz, CHL0R0F0RM- d) delta ppm 1.35 (s, 12 H) 4.03 (br. s., 2 H) 7.40 (d, J=1.61 Hz, 1 H) 8.14 (d, J=1.61 Hz, 1 H).

  • 2
  • [ 195457-53-5 ]
  • [ 1073354-96-7 ]
  • [ 1952236-05-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / 100 °C / Sealed tube; Microwave irradiation 2: pyridine / 20 °C
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 1073354-96-7 ]

Organoboron

Chemical Structure| 1310383-11-9

[ 1310383-11-9 ]

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

Similarity: 0.88

Chemical Structure| 444120-94-9

[ 444120-94-9 ]

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

Similarity: 0.86

Chemical Structure| 452972-11-1

[ 452972-11-1 ]

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

Similarity: 0.85

Chemical Structure| 1310404-51-3

[ 1310404-51-3 ]

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

Similarity: 0.84

Chlorides

Chemical Structure| 1310383-11-9

[ 1310383-11-9 ]

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

Similarity: 0.88

Chemical Structure| 444120-94-9

[ 444120-94-9 ]

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

Similarity: 0.86

Chemical Structure| 452972-11-1

[ 452972-11-1 ]

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

Similarity: 0.85

Chemical Structure| 1310404-51-3

[ 1310404-51-3 ]

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

Similarity: 0.84

Chemical Structure| 1073371-78-4

[ 1073371-78-4 ]

2,6-Dichloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.84

Esters

Chemical Structure| 1310383-11-9

[ 1310383-11-9 ]

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

Similarity: 0.88

Chemical Structure|

[ ]

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

Similarity: 0.87

Chemical Structure| 444120-94-9

[ 444120-94-9 ]

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

Similarity: 0.86

Chemical Structure| 452972-11-1

[ 452972-11-1 ]

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

Similarity: 0.85

Chemical Structure|

[ ]

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

Similarity: 0.84

Related Parent Nucleus of
[ 1073354-96-7 ]

Pyridines

Chemical Structure| 1310383-11-9

[ 1310383-11-9 ]

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

Similarity: 0.88

Chemical Structure| 444120-94-9

[ 444120-94-9 ]

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

Similarity: 0.86

Chemical Structure| 452972-11-1

[ 452972-11-1 ]

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

Similarity: 0.85

Chemical Structure| 1310404-51-3

[ 1310404-51-3 ]

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

Similarity: 0.84

Chemical Structure| 1073371-78-4

[ 1073371-78-4 ]

2,6-Dichloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Similarity: 0.84