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Chemical Structure| 1609374-04-0 Chemical Structure| 1609374-04-0

Structure of 1609374-04-0

Chemical Structure| 1609374-04-0
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Product Details of [ 1609374-04-0 ]

CAS No. :1609374-04-0
Formula : C18H20BNO3
M.W : 309.17
SMILES Code : CC1(C)C(C)(C)OB(C2=C3C(C4=CC=C(C)N=C4O3)=CC=C2)O1
MDL No. :MFCD32640809
InChI Key :FPPVNLSNFDMQGR-UHFFFAOYSA-N
Pubchem ID :90121488

Safety of [ 1609374-04-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 1609374-04-0 ]

* 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 [ 1609374-04-0 ]

[ 1609374-04-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 42260-39-9 ]
  • [ 1609374-04-0 ]
  • [ 1609374-06-2 ]
YieldReaction ConditionsOperation in experiment
82% With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); XPhos; In water; ethyl acetate; toluene;Inert atmosphere; Reflux; 2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine (5.96 g, 19.28 mmol), <strong>[42260-39-9]2-chloro-4-phenylpyridine</strong> (4.39 g, 23.13 mmol),tris(dibenzylideneacetone)palladium(0) (0.353 g, 0.386 mmol) and 2-Dicyclohexylphosphino-2?,6?-dimethoxybiphenyl (.8g, 1.951 mmol) were charged into a 500 mL 2-neck flask. Potassium phosphate tribasic (12.26 g, 57.8 mmol) was thendissolved in 45 mL of water. This solution was charged into the reaction mixture. The reaction mixture was degassedwith nitrogen then was heated to reflux overnight. The reaction mixture was cooled to room temperature. The toluenelayer was separated and was dried over magnesium sulfate. These organics were filtered and concentrated undervacuum. The crude product was passed through a silica gel column using 70-99percent toluene/ heptanes followed by 5-15percentethyl acetate/ toluene. Some of the impure product fractions were columned on silica gel using 5-15percent ethyl acetate/DCM. All the clean product fractions were combined yielding 2-methyl-8-(4-phenylpyridin-2-yl)benzofuro[2,3-b]pyridine(5.3 g, 15.76 mmol, 82 percent yield).
78% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); In water; toluene;Inert atmosphere; Reflux; A mixture of 2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine (4.34 g, 14.03 mmol), <strong>[42260-39-9]2-chloro-4-phenylpyridine</strong> (2.66 g,14.03 mmol), Pd2(dba)3 (0.257 g 0.281 mmol), dicyclohexyl(2?,6?-dimethoxy-[1,1?-biphenyl]-2-yl)phosphine (0.582 g,1.42 mmol), potassium phosphate (8.93 g, 42.1 mmol), toluene (180 mL) and water (28 mL) was degassed with nitrogenand then refluxed overnight. The mixture was concentrated and extracted with ethyl acetate. The ethyl acetate layerwas dried on Na2SO4 and then further purified by column chromatography using ethyl acetate in hexanes to give 2-methyl-8-(4-phenylpyridin-2-yl)benzofuro[2,3-b]pyridine (3.66 g, 10.88 mmol, 78 percent yield).
 

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