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Chemical Structure| 459856-12-3 Chemical Structure| 459856-12-3

Structure of 459856-12-3

Chemical Structure| 459856-12-3

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Product Details of [ 459856-12-3 ]

CAS No. :459856-12-3
Formula : C7H10BNO3
M.W : 166.97
SMILES Code : CC1=NC(OC)=CC=C1B(O)O
MDL No. :MFCD05662386
InChI Key :CWXWIICBKIHZFC-UHFFFAOYSA-N
Pubchem ID :2763084

Safety of [ 459856-12-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H315-H318-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P312-P305+P351+P338+P310-P332+P313-P362-P403+P233-P405-P501
Class:8
UN#:3261
Packing Group:

Application In Synthesis of [ 459856-12-3 ]

* 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 [ 459856-12-3 ]

[ 459856-12-3 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 126717-59-7 ]
  • [ 459856-12-3 ]
YieldReaction ConditionsOperation in experiment
(3) The synthesis of 6-methoxy-2-methylpyridine-3-boronic acid 21.2g of <strong>[126717-59-7]3-bromo-6-methoxy-2-methylpyridine</strong> was dissolved in 100ml of anhydrous tetrahydrofuran, 79ml of n-butyllithium (1.6M hexane solution) was added dropwise for 30 minutes at -70 C under nitrogen atmosphere. After dropping, stirring was carried out for 30 minutes at -70 C, a solution of 37ml of triisopropyl borate in 50ml of anhydrous tetrahydrofuran was added dropwise for 40 minutes at -70 C. After completion of dropping, dry ice-acetone bath was removed, which was stirred for 16 hours at room temperature. Afterwards, 12ml of acetic acid was added at room temperature followed by stirring for another hour. Water and ethyl acetate were added to reaction liquid, and the organic layer was separated. The resulting organic layer was washed with brine and then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure, and recrystallized from diethyl ether to give 6.31g of the title compound.
  • 2
  • [ 5419-55-6 ]
  • [ 126717-59-7 ]
  • [ 459856-12-3 ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; acetic acid; In tetrahydrofuran; hexane; water; isopropyl alcohol; D. 6-Methoxy-2-methylpyridine-3-boronic acid A solution of 6-methoxy-3-bromo-2-methylpyridine (59.8 g, 296 mmol) in dry THF (429 mL) was cooled with stirring to ~-78 C. under a nitrogen atmosphere. A solution of n-butyl lithium (2.5 M, 130.4 mL, 326 mmol) in hexane was added dropwise over 30 min. The reaction mixture was stirred for 3 h at ~-78 C. A solution of tri-isopropyl borate (102.7 mL, 445 mmol) in dry THF (100 mL) was added dropwise over 30 min. The reaction mixture was warmed to ambient temperature with stirring over 16 h. Acetic acid (37.35 g, 622 mmol), then water (110 mL) were added to the reaction mixture with stirring. After 2 h, the layers were separated and the organic layer was concentrated in vacuo. The residue was taken up in 2-propanol (750 mL) and solvent was removed on a rotary evaporator (bath temperature ~50 C.). The residue was triturated with ether. The product was collected by filtration and dried in vacuo (48.4 g): mp>200 C.; 1H-NMR(CD3OH, 300 MHz): delta 7.83 (d, 1H, J=8), 6.56 (d, 1H, J=8), 3.85 (s, 3H), 2.44 (s, 3H); GC-MS: 168 (M++H).
  • 3
  • [ 1000342-95-9 ]
  • [ 76-05-1 ]
  • [ 459856-12-3 ]
  • 4-(6-methoxy-2-methylpyridin-3-yl)-6-(trifluoromethyl)-1H-indazole trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% EXAMPLE 249: 4-(6-methoxy-2-methylpyridin-3-yl)-6-(trifluoromethyl)-lH- indazole [0790] A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-lH-indazole (0.15 g, 0.566 mmol), (6-methoxy-2-methylpyridin-3-yl)boronic acid (0.123 g, 0.736 mmol) and PdCl2(dppf) (0.021 g, 0.028 mmol) in dioxane (10 mL) and aqueous saturated NaHC03 (3 mL). The resulting light brown suspension was heated at 140°C for 45 minutes in microwave reactor. The reaction mixture was subsequently concentrated and the crude residue was purified by preparative HPLC, eluting with 45percent ACN (containing 0.035percent) TFA) in H20 (containing 0.05percent TFA) over a period of 6.5 minutes. The volatiles were removed in vacuo to give a TFA salt of the title compound as a light brown oil (82 mg, 47percent). 1H NMR (400 MHz, OMSO-de) delta ppm 2.30 (s, 3 H), 3.93 (s, 3 H), 6.75-6.86 (m, 1 H), 7.29 (d, J=1.26 Hz, 1 H), 7.72 (d, J=8.34 Hz, 1 H), 7.90-8.03 (m, 2 H); ESI-MS m/z [M+H]+ calc'd for Ci5Hi2F3N30, 308.1; found 308.15.
 

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Technical Information

Categories

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[ 459856-12-3 ]

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