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Structure of 1246372-66-6

Chemical Structure| 1246372-66-6

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Product Details of [ 1246372-66-6 ]

CAS No. :1246372-66-6
Formula : C12H16BN3O2
M.W : 245.09
SMILES Code : N#CC1=C(N)N=CC(B2OC(C)(C)C(C)(C)O2)=C1
MDL No. :MFCD16995200
InChI Key :KRNXYPYYVHFVQS-UHFFFAOYSA-N
Pubchem ID :67283616

Safety of [ 1246372-66-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 1246372-66-6 ]

* 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 [ 1246372-66-6 ]

[ 1246372-66-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 709652-82-4 ]
  • [ 73183-34-3 ]
  • [ 1246372-66-6 ]
YieldReaction ConditionsOperation in experiment
66% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 100℃; for 2h;Inert atmosphere; 8.2 Boronate 10: Compound 9 (50 g, 0.224 mol),bis (pinacolato) diboron (85.6 g, 0.337 mol), KOAc (44.1 g, 0.449 mol) and Pd (dppf) Cl2. CH2C12 (2.77 g, 3.4 mmol) were charged into a flask. Dioxane (400 mL) was added. Thereaction mixture was stirred at 100C for 2 hr under Ar. When LC-MS indicated that the reaction was completed, the mixture was cooled to room temperature. The mixture was filtered through diatomite, concentrated, diluted with a mixture of ethyl acetate and hexane in 3/1 ratio (1000 mL) , filtered through silica gel (300-400 mesh) , concentrated, crystallized and dried to give boronate 10 (32 g, 66%) as a white solid
66% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 100℃; for 2h;Inert atmosphere; Boronate 10: Compound 9 (50 g, 0.224 mol), bis(pinacolato)diboron (85.6 g, 0.337 mol), KOAc (44.1 g, 0.449 mol) and Pd(dppf)Cl2.CH2Cl2 (2.77 g, 3.4 mmol) were charged into a flask. Dioxane (400 mL) was added. The reaction mixture was stirred at 100 C. for 2 hr under Ar. When LC-MS indicated that the reaction was completed, the mixture was cooled to room temperature. The mixture was filtered through diatomite, concentrated, diluted with a mixture of ethyl acetate and hexane in 3/1 ratio (1000 mL), filtered through silica gel (300-400 mesh), concentrated, crystallized and dried to give boronate 10 (32 g, 66%) as a white solid.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In acetonitrile; at 150℃; for 0.25h;Microwave irradiation; To a microwave vial equipped with a stirbar was dissolve <strong>[709652-82-4]2-amino-5-bromonicotinonitrile</strong> (0.087 g, 0.44 mmol) in anhydrous acetonitrile (4 mL). To the solution was added potassium acetate(0.086 g, 0.86 mmol), 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane (0.223 g, 0.86 mmol) and 1,1 ?-bis(diphenylphosphino)ferrocene-palladium(ll)dichloride (0.016 g, 0.022 mmol). The resulting mixture was microwaved at 150 C for 15 mm. To the mixture was added (1R,5S,6r)-6-(3-iodo- 1 -isopropyl- 1H-pyrazol-5-yl)-3-(oxetan-3-yl)-3-azabicyclo[3.1 .0]hexane (0.100 g, 0.26 mmol), 1M potassium carbonate (4 mL) and further1,1 ?-bis(diphenylphosphino)ferrocene-palladium(ll)dichloride (0.008 g, 0.011 mmol) and the resulting mixture was microwave at 110 C for 15 mm. The reaction mixture was diluted with 10 mL water and extracted with ethyl acetate (3 x 15 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated to dryness in vacuo. This crude material was purified by RP-HPLC affording2-amino-5-(1 -isopropyl-5-((1R,5S,6r)-3-(oxetan-3-yl)-3-azabicyclo[3. 1 .0]hexan-6-yl)-1H-pyrazol-3-yl)nicotinonitrile (20.1mg, 21%): ?H NMR (400MHz, DMSO-d6) oe: 8.57 (s, 1H), 8.08 (s, 1H), 6.91(s, 2H), 6.35 (s, 1H), 4.73 -4.62 (m, 1H), 4.60-4.44 (m, 4H), 3.81 - 3.70 (m, 1H), 3.12 (d, J = 8.8Hz, 2H), 2.46-2.39 (m, 2H), 2.19-2.12 (m, 1H), 1.82- 1.76 (m, 2H), 1.42 (d, J = 6.5 Hz, 6H).
  • 2
  • [ 709652-82-4 ]
  • [ 73183-34-3 ]
  • [ 1246372-66-6 ]
  • (6-amino-5-cyanopyridin-3-yl)boronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,2-dimethoxyethane; at 90℃; for 3h;Microwave irradiation; Inert atmosphere; Example 126 Step 1: (6-amino-5-cyanopyridin-3-yl)boronic acid and 2-amino-5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)nicotinonitrile To a stirred solution of <strong>[709652-82-4]2-amino-5-bromonicotinonitrile</strong> (100 mg, 0.51 mmol) and 1,2- dimethoxyethane (4 mL) in a microwave vial equipped with a stirbar was added bis(pinacolato diborane) (175 mg, 0.66 mmol), potassium acetate (149 mg, 1.52 mmol) and 1,1'- bis(diphenylphosphino)ferrocene-palladium(II)dichloride (21 mg, 0.025 mmol). The mixture was purged with nitrogen gas for 5 min and the reaction mixture was stirred at 90 C for 3 h. The reaction mixture was filtered through a celite bed and washed with dichloromethane (10 mL). The filtrate was concentrated to dryness in vacuo affording a crude mixture of (6-amino-5-cyanopyridin-3-yl)boronic acid and 2-amino-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)nicotinonitrile used for the next step without any further purification.
 

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[ 1246372-66-6 ]

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Related Parent Nucleus of
[ 1246372-66-6 ]

Pyridines

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