792909-35-4|N-Phenyl-N-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)naphthalen-1-amine| Ambeed

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CAS No. :	792909-35-4
Formula :	C₃₄H₃₂BNO₂
M.W :	497.43
SMILES Code :	CC1(C)C(C)(C)OB(C2=CC=C(C3=CC=C(N(C4=CC=CC=C4)C5=C6C=CC=CC6=CC=C5)C=C3)C=C2)O1

Yield	Reaction Conditions	Operation in experiment
90%	With potassium acetate;Pd(dppf)Cl2; In 1,4-dioxane; ethyl acetate;	Example 1.2.1 N-phenyl-N-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)naphthalen-1-amine (5): A mixture of Compound 4 (5.5 g, 12.2 mmol), bis(pinacolate)diborane (3.10 g, 12.2 mmol), Pd(dppf)Cl2 (0.446 mg, 0.6 mmol) and KOAc (5.5 g, 56 mmol) in anhydrous dioxane (60 ml) was degassed and heated at 80 C. overnight. After being cooled to RT, the mixture was poured into ethyl acetate (200 ml), washed with brine (150 ml). The organic solution was dried over Na2SO4, loaded on silica gel and purified by flash column (hexanes to hexanes/ethyl acetate 30:1) to collect the major fraction. After removal of solvent, the solid was washed with methanol, filtered and dried in air to give a white solid 5 (5.50 g, in 90% yield).
90%	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃;	Example 1.2.2 N-phenyl-N-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)naphthalen-1-amine (7): A mixture of Compound 6 (5.5 g, 12.2 mmol), bis(pinacolate)diborane (3.10 g, 12.2 mmol), Pd(dppf)Cl2 (0.446 mg, 0.6 mmol) and KOAc (5.5 g, 56 mmol) in anhydrous dioxane (60 ml) was degassed and heated at 80 C. overnight. After being cooled to RT, the mixture was poured into ethyl acetate (200 ml), washed with brine (150 ml). The organic solution was dried over Na2SO4, loaded on silica gel and purified by flash column (hexanes to hexanes/ethyl acetate 30:1) to collect the major fraction. After removal of solvent, the solid was washed with methanol, filtered and dried in air to give a white solid 7 (5.50 g, in 90% yield).
90%	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃;	Example 1.2.14 5[0047] N-phenyl-N-(4'-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-[l,l'- biphenyl]-4-yl)naphthalen-l-amine (5): A mixture of Compound 4( 5.5 g, 12.2 mmol), bis(pinacolate)diborane (3.10 g, 12.2 mmol), Pd(dppf)Cl2 (0.446 mg, 0.6 mmol) and KOAc (5.5 g, 56 mmol) in anhydrous dioxane (60 ml) was degassed and heated at 80 C overnight. After being cooled to RT, the mixture was poured into ethyl acetate (200 ml), washed with brine (150 ml). The organic solution was dried over Na2S04, loaded on silica gel and purified by flash column (hexanes to hexanes/ethyl acetate 30:1) to collect the major fraction. After removal of solvent, the solid was washed with methanol, filtered and dried in air to give a white solid 5 (5.50g, in 90% yield).

90%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃;	A mixture of Compound 6 (5.5 g, 12.2 mmol), bis (pinacolate)diborane (3.10 g, 12.2 mmol), Pd(dppf)C12 (0.446 mg, 0.6 mmol) and KOAc (5.5 g, 56 mmol) in anhydrous dioxane (60 ml) was degassed and heated at 80 C. overnight. After being cooled to RT, the mixture was poured into ethyl acetate (200 ml), and washed with brine (150 ml). The organic solution was dried over Na2504, loaded on silica gel and purified by flash column (hexanes to hexanes/ethyl acetate 30:1) to collect the major fraction. After removal of solvent, the solid was washed with methanol, filtered and dried in air to give a white solid 7 (5.50 g, in 90% yield).
90%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃;Inert atmosphere;	Amixture of Compound 4(5.5 g, i2.2 mmol), bis(pinacolate)diborane (3.10 g, i2.2 mmol), Pd(dppf)C12 (0.446 mg,0.6 mmol) and KOAc (5.5 g, 56 mmol) in anhydrous dioxane(60 mE) was degassed and heated at about 80 C. overnight.After being cooled to RT, the mixture was poured into ethyl acetate (200 mE), and washed with brine (150 mE). The organic solution was dried over Na2SO4, loaded on silica gel and purified by flash column (hexanes to hexanes/ethyl acetate 30:1) to collect the major fraction. After removal ofsolvent, the solid was washed with methanol, filtered and dried in air to give a white solid CompoundS (5.50 g, in 90% yield).
90%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃;Inert atmosphere;	A mixture of Compound 5 (5.5 g, 12.2 mmol), bis(pinacolate)diborane (3.10 g, 12.2 mmol), Pd(dppf)C12(0.446 mg, 0.6 mmol) and KOAc (5.5 g, 56 mmol) inanhydrous dioxane (60 ml) was degassed and heated atabout 80 C. overnight. After being cooled to RT, themixture was poured into ethyl acetate (200 ml) and washedwith brine (150 ml). The organic solution was dried overNa2SO4, loaded on silica gel and purified by flash colunm(hexanes to hexanes/ethyl acetate 30:1) to collect the majorfraction. After removal of solvent, the solid was washed withmethanol, filtered and dried in air to give a white solid (5.50g, in 90% yield).

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CAS No.: 792909-35-4

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CAS No.: 792909-35-4

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[ 792909-35-4 ] Synthesis Path-Downstream 1~2

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H201	Explosive; mass explosion hazard
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H220	Extremely flammable gas
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H227	Combustible liquid
H228	Flammable solid
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
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