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[ CAS No. 863578-36-3 ] {[proInfo.proName]}

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Chemical Structure| 863578-36-3
Chemical Structure| 863578-36-3
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Product Details of [ 863578-36-3 ]

CAS No. :863578-36-3 MDL No. :MFCD06795679
Formula : C13H20BNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :PEXRISJTWBBZRY-UHFFFAOYSA-N
M.W :233.11 Pubchem ID :17750209
Synonyms :

Safety of [ 863578-36-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 863578-36-3 ]

* 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 [ 863578-36-3 ]

[ 863578-36-3 ] Synthesis Path-Downstream   1~56

  • 1
  • [ 863578-36-3 ]
  • [ 1352874-26-0 ]
  • [ 1352874-51-1 ]
YieldReaction ConditionsOperation in experiment
25% With sodium carbonate In 1,2-dimethoxyethane; water at 150℃; for 0.283333h; Microwave radiation; III.6.1 Step 1 : 4'-[3-(2-Chloro-benzyl)-2-imino-2,3-dihydro-benzoimidazol-1 -yl]-4-methyl- biphenyl-2-ylamineIntermediate M (100 mg, 0.241 mmol), 2-Amino-4-Methylphenylboronic acid pinacol ester ( Boron Molecular BM367) (63.1 mg, 0.265 mmol) and Pd(Ph3P)4 (14.2 mg, 12.1 μηηοΙ) were suspended in DME (1 .2 mL) and 2M aqueous Na2C03 solution (0.6 ml_, 1.20 mmol). The resulting reaction mixture was stirred for 17 minutes at 150°C under microwave irradiation. The reaction mixture was then diluted with MeOH (2 mL) and filtered through a pad of diatomaceous earth which was rinsed with EtOAc (2x4 mL). The resulting organic filtrate was evaporated to dryness and the crude product purified by reverse- phase preparative HPLC (Method E). Product-containing fractions were pooled and eva- porated to dryness to furnish the title compound as a TFA salt, 33 mg (25%). HPLC/MS (Method A) tR1.40 minute, M+H 339
  • 2
  • [ 109-04-6 ]
  • [ 863578-36-3 ]
  • [ 113623-79-3 ]
YieldReaction ConditionsOperation in experiment
With barium hydroxide octahydrate In 1,4-dioxane; water at 100℃; for 4h; Inert atmosphere;
  • 3
  • [ 863578-36-3 ]
  • [ 1393606-84-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: barium hydroxide octahydrate / 1,4-dioxane; water / 4 h / 100 °C / Inert atmosphere 2.1: acetic acid; sodium nitrite / water / 1.5 h / 0 °C / Inert atmosphere 2.2: 0.5 h / 20 °C / Inert atmosphere
  • 4
  • [ 863578-36-3 ]
  • [ 1393606-42-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: barium hydroxide octahydrate / 1,4-dioxane; water / 4 h / 100 °C / Inert atmosphere 2.1: acetic acid; sodium nitrite / water / 1.5 h / 0 °C / Inert atmosphere 2.2: 0.5 h / 20 °C / Inert atmosphere 3.1: dichloromethane / 20 °C / Inert atmosphere
  • 5
  • [ 53078-85-6 ]
  • [ 25015-63-8 ]
  • [ 863578-36-3 ]
YieldReaction ConditionsOperation in experiment
84% With bis-triphenylphosphine-palladium(II) chloride; triethylamine In 1,4-dioxane at 120℃; for 12h; Inert atmosphere;
82% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine In 1,4-dioxane at 120℃; for 12h;
68% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine In 1,4-dioxane at 120℃; for 12h; Inert atmosphere;
66% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine In 1,4-dioxane at 100℃; for 12h; Inert atmosphere;
46% With bis[1,2-bis(diphenylphosphino)ferrocene]-palladium(0); triethylamine In 1,4-dioxane at 100℃; for 12h;
With palladium diacetate; triethylamine; CyJohnPhos In 1,4-dioxane at 80℃; for 1h; Inert atmosphere;

  • 6
  • [ 30414-53-0 ]
  • [ 863578-36-3 ]
  • [ 1423076-86-1 ]
YieldReaction ConditionsOperation in experiment
38% With potassium chloride; oxygen; copper diacetate In methanol at 50℃;
  • 7
  • [ 30414-57-4 ]
  • [ 863578-36-3 ]
  • [ 1423076-87-2 ]
YieldReaction ConditionsOperation in experiment
40% With potassium chloride; oxygen; copper diacetate In methanol at 50℃;
  • 8
  • [ 863578-36-3 ]
  • [ 105-45-3 ]
  • [ 1082470-14-1 ]
YieldReaction ConditionsOperation in experiment
59% With potassium chloride; oxygen; copper diacetate In methanol at 50℃;
  • 9
  • [ 863578-36-3 ]
  • [ 57486-69-8 ]
  • [ 1434044-04-8 ]
YieldReaction ConditionsOperation in experiment
82% General procedure: To a 2-5 mL capacity microwave vial was charged <strong>[57486-69-8]methyl 2-(2-bromophenyl)acetate</strong> (0.100g, 0.43 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.115 g, 0.523 mmol)and cesium carbonate (0.280 g, 0.86 mmol) in anhydrous 1,2-dimethoxy ethane (4 mL). Themixture was stirred and degassed with argon for 5 min. To this mixture was added Pd(PPh3)4(25 mg, 0.021 mmol) under argon atmosphere, and purged for 2 min. The tube was sealedand irradiated in microwave at 125 C for 0.5 h (This is the internal temperature of reactionmixture and monitored on the screen through a sensor). The vial was cooled to 0C over aperiod of 15 min, followed by addition of 1M potassium tert-butoxide (0.65 mL, 0.65 mmol)solution in THF. The resulting mixture was stirred for 10 minutes and quenched withsaturated ammonium chloride solution. The mixture was diluted with ethyl acetate (30 mL)and washed with water and brine. The organic layer was dried over anhydrous sodiumsulfate, filtered and concentrated. The residue obtained was purified by flash columnchromatography by eluting with gradient of 2-20% ethyl acetate in hexane to afford the 5Hdibenzo[b,d]azepin-6(7H)-one (4) as off white solid (0.075 g, 82%).
  • 10
  • [ 863578-36-3 ]
  • [ 198630-93-2 ]
  • [ 1434044-11-7 ]
YieldReaction ConditionsOperation in experiment
81% Stage #1: 5-methyl-2-(4,4,5,5-tetramethyl)(1,3,2-dioxaborolan-2-yl)phenylamine; methyl 2-(2-bromo-4-methoxyphenyl)acetate With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,2-dimethoxyethane at 125℃; for 0.5h; Microwave irradiation; Inert atmosphere; Sealed tube; Stage #2: With potassium <i>tert</i>-butylate In tetrahydrofuran; 1,2-dimethoxyethane at 0 - 20℃; for 0.166667h; Inert atmosphere; Sealed tube; Condition 1: Synthesis of 5H-dibenzo[b,d]azepin-6(7H)-one (4) General procedure: To a 2-5 mL capacity microwave vial was charged methyl 2-(2-bromophenyl)acetate (0.100g, 0.43 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.115 g, 0.523 mmol)and cesium carbonate (0.280 g, 0.86 mmol) in anhydrous 1,2-dimethoxy ethane (4 mL). Themixture was stirred and degassed with argon for 5 min. To this mixture was added Pd(PPh3)4(25 mg, 0.021 mmol) under argon atmosphere, and purged for 2 min. The tube was sealedand irradiated in microwave at 125 °C for 0.5 h (This is the internal temperature of reactionmixture and monitored on the screen through a sensor). The vial was cooled to 0°C over aperiod of 15 min, followed by addition of 1M potassium tert-butoxide (0.65 mL, 0.65 mmol)solution in THF. The resulting mixture was stirred for 10 minutes and quenched withsaturated ammonium chloride solution. The mixture was diluted with ethyl acetate (30 mL)and washed with water and brine. The organic layer was dried over anhydrous sodiumsulfate, filtered and concentrated. The residue obtained was purified by flash columnchromatography by eluting with gradient of 2-20% ethyl acetate in hexane to afford the 5Hdibenzo[b,d]azepin-6(7H)-one (4) as off white solid (0.075 g, 82%).
  • 11
  • [ 863578-36-3 ]
  • [ 1579291-80-7 ]
YieldReaction ConditionsOperation in experiment
62% With 2-Methyl-2-nitropropane; trimethylsilylazide In acetonitrile at 0 - 20℃; for 1.5h; Inert atmosphere;
62% With tert.-butylnitrite; trimethylsilylazide In acetonitrile at 20℃; for 1h;
46% With 2-Methyl-2-nitropropane; trimethylsilylazide In acetonitrile at 0 - 20℃; for 1.5h; Inert atmosphere;
  • 12
  • [ 863578-36-3 ]
  • [ 1579291-57-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2-Methyl-2-nitropropane; trimethylsilylazide / acetonitrile / 1.5 h / 0 - 20 °C / Inert atmosphere 2: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate / water; tetrahydrofuran / 1.5 h / 80 °C / Inert atmosphere
  • 13
  • [ 863578-36-3 ]
  • [ 1579291-67-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 2-Methyl-2-nitropropane; trimethylsilylazide / acetonitrile / 1.5 h / 0 - 20 °C / Inert atmosphere 2: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate / water; tetrahydrofuran / 1.5 h / 80 °C / Inert atmosphere 3: bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)] / toluene / 16 h / 80 °C / Inert atmosphere
  • 14
  • [ 863578-36-3 ]
  • 2-azido-4-methylphenyllead acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trimethylsilylazide; 2-Methyl-2-nitropropane / acetonitrile / 1.5 h / 0 - 20 °C / Inert atmosphere 2: mercury(II) diacetate / chloroform / 16 h / 50 °C / Inert atmosphere
  • 15
  • [ 863578-36-3 ]
  • [ 1611447-09-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trimethylsilylazide; 2-Methyl-2-nitropropane / acetonitrile / 1.5 h / 0 - 20 °C / Inert atmosphere 2: mercury(II) diacetate / chloroform / 16 h / 50 °C / Inert atmosphere 3: pyridine / chloroform / 12 h / 50 °C / Inert atmosphere
  • 16
  • [ 863578-36-3 ]
  • [ 1611447-15-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trimethylsilylazide; 2-Methyl-2-nitropropane / acetonitrile / 1.5 h / 0 - 20 °C / Inert atmosphere 2: mercury(II) diacetate / chloroform / 16 h / 50 °C / Inert atmosphere 3: pyridine / chloroform / 12 h / 50 °C / Inert atmosphere
  • 17
  • [ 1188365-78-7 ]
  • [ 863578-36-3 ]
  • C22H20N4OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane at 100℃; for 6h; 3 Compound 3: (R)-3-chloro-10-methyl-9,10,l l,12-tetrahydro-8H-[l,4]diazepino [5',6':4,5]thieno[3,2-f]quinolin-8-one (intermediate 11, Ex 51; 100 mg, 0.3 mmol) in dioxane (10.0 mL) was treated with 5-methyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (320 mg, 0.9 mmol), sodium carbonate (100 mg, 0.9 mmol) and tetrakis (triphenylphosphine) palladium (75 mg, 0.06 mmol). The resulting mixture was heated at 100 °C for 6 h. After completion of the reaction, the solvent was removed under reduced pressure. The resulting residue was filtered through ceiite and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and triturated with diethyl ether to afford 3 (101 mg, 83%) as a yellow solid. MS m/z (M+H): 389.6
  • 18
  • [ 1188365-78-7 ]
  • [ 863578-36-3 ]
  • (R)-N-(5-methyl-2-(10-methyl-8-oxo-9,10,11,12-tetrahydro-8H-[1,4]diazepino[5',6':4,5]thieno[3,2-f]quinolin-3-yl)phenyl)acrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 6 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / acetone / 1 h / 0 - 20 °C
  • 19
  • [ 53078-85-6 ]
  • [ 73183-34-3 ]
  • [ 863578-36-3 ]
YieldReaction ConditionsOperation in experiment
17% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In dimethyl sulfoxide at 110℃; for 6h; 2 5-methyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (2): 5-methyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (2): A solution of 2-bromo-5-methylani fine (1.5 g, 8.0 mmol) in dimethyl sulfoxide (20.0 mL) was treated with bis-pinacolatodiborane(2.4 g, 9.7mmol), potassium acetate (2.4 g, 24 mmol), and [1,1 'Bis(diphenylphosphino)ferrocene] dichloropalladium(II) complex with dichloromethane (329 mg, 0.04 mmol) at 110 °C for 6 h. After completion of the reaction, the reaction mixture was filtered through celite and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to afford 2 (320 mg, 17%) as a pale yellow liquid. 1H NMR (400 MHz, DMSO-d6): δ 1.26 (s, 12H), 2.13 (s, 3H), 5.37 (s, 2H), 6.29 (d, J = 7.5 Hz, 1H), 6.37 (s, 1H), 7.23 (d, J = 7.5 Hz, 1H). MS m/z (M+H): 234.2
  • 20
  • [ 5326-34-1 ]
  • [ 863578-36-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ammonium chloride; zinc / 1,4-dioxane; water / 3 h / 20 °C 2: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / dimethyl sulfoxide / 6 h / 110 °C
  • 21
  • [ 863578-36-3 ]
  • methyl-2-(2-azido-4-methylphenyl)cyclohex-1-enecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trimethylsilylazide; tert.-butylnitrite / acetonitrile / 1 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate / 1,2-dimethoxyethane; water / 1 h / 100 °C
  • 22
  • [ 863578-36-3 ]
  • methyl-7-methyl-2,3,4,4a-tetrahydro-1H-carbazole-4a-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trimethylsilylazide; tert.-butylnitrite / acetonitrile / 1 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate / 1,2-dimethoxyethane; water / 1 h / 100 °C 3: bis[rhodium(alpha,alpha,alpha’,alpha′-tetramethyl-1,3-benzenedipropionic acid)] / toluene / 16 h / 140 °C
  • 23
  • [ 863578-36-3 ]
  • [ 762-42-5 ]
  • C13H14BNO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% In 1,2-dichloro-ethane at 110℃; for 0.5h; Microwave irradiation;
  • 24
  • [ 863578-36-3 ]
  • [ 762-42-5 ]
  • C13H14BNO5 [ No CAS ]
  • C19H26BNO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 52% 2: 35% In dichloromethane at 80℃;
  • 25
  • [ 863578-36-3 ]
  • [ 762-42-5 ]
  • [ 1169879-60-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1,2-dichloro-ethane / 0.5 h / 110 °C / Microwave irradiation 2: palladium diacetate / 1,2-dichloro-ethane / 0.5 h / 80 °C / Sealed tube
Multi-step reaction with 2 steps 1: dichloromethane / 80 °C 2: palladium diacetate / 1,2-dichloro-ethane / 0.5 h / 80 °C / Sealed tube
  • 26
  • [ 863578-36-3 ]
  • C31H30BrN2O(1+)*Cl(1-) [ No CAS ]
  • [ 76-05-1 ]
  • 16-[4-(2-amino-4-methylphenyl)phenyl]-3-oxa-9λ5,23-diazaheptacyclo[17.7.1.15,9.02,17.04,15.023,27.013,28]octacosa-1(27),2(17),4,9(28),13,15,18-heptaen-9-ylium 2,2,2-trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5-methyl-2-(4,4,5,5-tetramethyl)(1,3,2-dioxaborolan-2-yl)phenylamine; C31H30BrN2O(1+)*Cl(1-) With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In ethanol; dichloromethane at 65℃; for 1h; Stage #2: trifluoroacetic acid In methanol; ethanol; dichloromethane; acetonitrile at 35℃; for 0.05h; 21 Preparation of a 4-carboxrhodamine trifluoroacetate (Compound 16) Example 21 ;Preparation of a 4-carboxrhodamine trifluoroacetate (Compound 16) ;The following compound is prepared: ;Compound 16 is 16-[4-(2-amino-4-methylphenyl)phenyl]-3-oxa-9λ5,23-diazaheptacyclo[17.7.1.15,9.02,17.04,15.023,27.013,28]octacosa-1(27),2(17),4,9(28),13,15,18-heptaen-9-ylium; 2,2,2-trifluoroacetate according to the nomenclature system that we use and is prepared as follows. Intermediate 4 (152 mg, 0.29 mmol) and 5-methyl-2-(4,4,5,5-tetramethyl)-(1,3,2-dioxaborolan-2-yl)-phenylamine (135 mg, 0.58 mmol) are dissolved in ethanol (10 mL) and treated with 2M K2CO3 (434 μL, 0.87 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) DCM (11 mg, 0.015 mmol). The reaction mixture is heated at 65° C. for 1 hour. The crude product is filtered through celite and purified on an ACE-C8 (150*30 mm) column eluting with 60-100% methanol in 0.1% TFA, evaporating pure fractions to 80 mg (50% yield) deep blue/red solid with a green tinge. Purity as determined by HPLC is 90%. MS (ESI) [M+]=552. Absorbance max is 580 nm.
  • 27
  • [ 863578-36-3 ]
  • [ 89-98-5 ]
  • [ 1859-13-8 ]
YieldReaction ConditionsOperation in experiment
89% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In dimethyl sulfoxide at 120℃; for 8h; Inert atmosphere;
  • 28
  • [ 863578-36-3 ]
  • C17H10Br2O2 [ No CAS ]
  • C31H22N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With bis-triphenylphosphine-palladium(II) chloride; sodium t-butanolate In toluene at 110℃; for 3h; Inert atmosphere;
  • 29
  • [ 577-19-5 ]
  • [ 863578-36-3 ]
  • 4-methyl-2'-nitro-[1,1'-biphenyl]-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,2-dimethoxyethane; water at 90℃; for 12h; Schlenk technique; Inert atmosphere;
  • 30
  • [ 863578-36-3 ]
  • C28H21IN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 12 h / 90 °C / Schlenk technique; Inert atmosphere 2.1: hydrogenchloride / water / 60 - 70 °C 2.2: 0.5 h / 5 °C 2.3: 6 h / Reflux 3.1: hydrogenchloride; tin(ll) chloride / water; ethanol / 7 h / Reflux 4.1: 5 h / Reflux 4.2: 2 h / 0 - 20 °C 5.1: palladium diacetate; potassium carbonate / water; dimethyl sulfoxide / 23 °C / Inert atmosphere; Schlenk technique
  • 31
  • [ 863578-36-3 ]
  • 2-iodo-4-methyl-2'-nitro-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 12 h / 90 °C / Schlenk technique; Inert atmosphere 2.1: hydrogenchloride / water / 60 - 70 °C 2.2: 0.5 h / 5 °C 2.3: 6 h / Reflux
  • 32
  • [ 863578-36-3 ]
  • 2'-iodo-4'-methyl-[1,1'-biphenyl]-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 12 h / 90 °C / Schlenk technique; Inert atmosphere 2.1: hydrogenchloride / water / 60 - 70 °C 2.2: 0.5 h / 5 °C 2.3: 6 h / Reflux 3.1: hydrogenchloride; tin(ll) chloride / water; ethanol / 7 h / Reflux
  • 33
  • [ 863578-36-3 ]
  • 2-iodo-2'-isocyano-4-methyl-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 12 h / 90 °C / Schlenk technique; Inert atmosphere 2.1: hydrogenchloride / water / 60 - 70 °C 2.2: 0.5 h / 5 °C 2.3: 6 h / Reflux 3.1: hydrogenchloride; tin(ll) chloride / water; ethanol / 7 h / Reflux 4.1: 5 h / Reflux 4.2: 2 h / 0 - 20 °C
  • 34
  • [ 863578-36-3 ]
  • (2-methyl-9H-carbazol-9-yl)(8-methylphenanthridin-6-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 12 h / 90 °C / Schlenk technique; Inert atmosphere 2.1: hydrogenchloride / water / 60 - 70 °C 2.2: 0.5 h / 5 °C 2.3: 6 h / Reflux 3.1: hydrogenchloride; tin(ll) chloride / water; ethanol / 7 h / Reflux 4.1: 5 h / Reflux 4.2: 2 h / 0 - 20 °C 5.1: palladium diacetate; potassium carbonate / water; dimethyl sulfoxide / 23 °C / Inert atmosphere; Schlenk technique 6.1: potassium carbonate; copper(l) iodide / dimethyl sulfoxide / 0.5 h / 23 °C / Inert atmosphere; Schlenk technique
  • 35
  • [ 863578-36-3 ]
  • [ 137058-15-2 ]
  • 6'-methyl-2'-phenylspiro[cyclopentane-1,3'-indole] [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate / water; 1,2-dimethoxyethane / 2 h / 100 °C / Inert atmosphere 2: trifluoroacetic acid; bis-[(trifluoroacetoxy)iodo]benzene / 2,2,2-trifluoroethanol / 3 h / 0 - 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate / water; 1,2-dimethoxyethane / 2 h / 100 °C / Inert atmosphere 2: iodobenzene; trifluoroacetic acid; Selectfluor / water / 3 h / 25 °C / Inert atmosphere
  • 36
  • [ 863578-36-3 ]
  • [ 137058-15-2 ]
  • 4-methyl-3',4',5',6'-tetrahydro-[1,1':2',1''-terphenyl]-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,2-dimethoxyethane; water at 100℃; for 2h; Inert atmosphere;
  • 37
  • [ 863578-36-3 ]
  • 2-chloro-5,5,9-trimethyl-7H-pyrido[2,3-d][1]benzazepin-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / 1,4-dioxane / 9 h / 120 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / 1,4-dioxane / 4 h / 0 - 20 °C
  • 38
  • [ 863578-36-3 ]
  • 2-chloro-5,5,9-trimethyl-7-[4-[2-(tetrahydropyran-4-ylamino)ethylamino]phenyl]pyrido[2,3-d][1]benzazepin-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / 1,4-dioxane / 9 h / 120 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / 1,4-dioxane / 4 h / 0 - 20 °C 3: potassium carbonate; trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 12 h / 20 °C
  • 39
  • [ 863578-36-3 ]
  • C34H41ClN4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / 1,4-dioxane / 9 h / 120 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / 1,4-dioxane / 4 h / 0 - 20 °C 3: potassium carbonate; trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere
  • 40
  • [ 863578-36-3 ]
  • methyl 2-(3-bromo-5-chloropyridin-2-yl)-2-methylpropanoate [ No CAS ]
  • C17H19ClN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane at 120℃; for 9h; Inert atmosphere; 4.1.32. 2,9-Dichloro-5,5-dimethyl-7H-pyrido[2,3-d][1]benzazepin-6-one(52) General procedure: To a solution of methyl 2-(3-bromo-5-chloro-2-pyridyl)-2-methylpropanoate(43) (2.21 g, 7.55 mmol) in 1,4-dioxane (25 mL) wereadded 5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline(2.49 g, 9.82 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (432 mg, 0.529 mmol), and cesium carbonate (4.92 g, 15.1 mmol) under N2. After being heated with stirring at refluxfor 9 h, the reaction mixture was filtered through a pad of Celite. Thefiltrate was concentrated in vacuo. The residual oil was dissolved in 1,4-dioxane (25 mL), and potassium tert-butoxide (1.70 g, 15.1 mmol) wasadded thereto at 0 °C. After being stirred at room temperature for 4 h,the reaction mixture was quenched with acetic acid (0.9 mL) andconcentrated in vacuo to give the crystals, which were collected byfiltration and washed with CH2Cl2 to give 52 as a pale brown solid(2.32 g, 6.35 mmol, 84% for two steps). 1H NMR (DMSO-d6) δ: 10.54(1H, s), 8.69 (1H, d, J = 1.8 Hz), 8.19 (1H, d, J = 2.4 Hz), 7.80 (1H, d,J = 8.5 Hz), 7.34 (1H, dd, J = 8.5, 1.8 Hz), 7.27 (1H, d, J = 1.8 Hz),1.64 (3H, br s), 1.03 (3H, br s). LC/MS m/z 308 (M + H)+.
  • 41
  • [ 1730-04-7 ]
  • [ 863578-36-3 ]
  • 7,9-dimethyl-7H-benzo[kl]acridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / dimethyl sulfoxide / 18 h / 80 °C 2: potassium carbonate / dimethyl sulfoxide / 24 h / 20 °C
  • 42
  • [ 1730-04-7 ]
  • [ 863578-36-3 ]
  • 2-(8-iodonaphthalen-1-yl)-5-methylaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In dimethyl sulfoxide at 80℃; for 18h; 2-(8-Iodonaphthalen-1-yl)aniline (1a). Typical Procedure General procedure: A mixture of diiodonaphthalene (428 mg, 1.13 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (247 mg, 1.13 mmol), Pd(PPh3)4 (65.1 mg, 0.0563 mmol), K3PO4 (717 mg, 3.38 mmol), DMSO(5.6 mL) were heated at 80 °C for 18 h. After cooling to rt, the reaction was stopped by adding H2O. The crude mixture was extracted with EtOAc (3 ×) and the combined organic extracts were washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by column chromatography (silica gel, hexane/EtOAc 6:1 containing1% Et3N) to give 1a as brown oil; yield: 180 mg (46%).
  • 43
  • [ 5177-27-5 ]
  • [ 863578-36-3 ]
  • C11H11ClN4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; XPhos In 1,4-dioxane at 100℃; for 4h;
  • 44
  • [ 863578-36-3 ]
  • C23H25N7O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; XPhos; sodium carbonate / 1,4-dioxane / 4 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 1 h / 20 °C 3: XPhos; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate / 1,4-dioxane / 2 h / 100 °C
  • 45
  • [ 863578-36-3 ]
  • C24H27N7O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; XPhos; sodium carbonate / 1,4-dioxane / 4 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 1 h / 20 °C 3: XPhos; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate / 1,4-dioxane / 2 h / 100 °C
  • 46
  • [ 863578-36-3 ]
  • C25H29N7O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; XPhos; sodium carbonate / 1,4-dioxane / 4 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 1 h / 20 °C 3: XPhos; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate / 1,4-dioxane / 2 h / 100 °C
  • 47
  • [ 863578-36-3 ]
  • C25H29N7O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; XPhos; sodium carbonate / 1,4-dioxane / 4 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 1 h / 20 °C 3: XPhos; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate / 1,4-dioxane / 2 h / 100 °C
  • 48
  • [ 863578-36-3 ]
  • C24H26FN7O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; XPhos; sodium carbonate / 1,4-dioxane / 4 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 1 h / 20 °C 3: XPhos; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate / 1,4-dioxane / 2 h / 100 °C
  • 49
  • [ 863578-36-3 ]
  • C24H26FN7O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; XPhos; sodium carbonate / 1,4-dioxane / 4 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 1 h / 20 °C 3: XPhos; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate / 1,4-dioxane / 2 h / 100 °C
  • 50
  • [ 863578-36-3 ]
  • C25H28N6O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; XPhos; sodium carbonate / 1,4-dioxane / 4 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 1 h / 20 °C 3: XPhos; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate / 1,4-dioxane / 2 h / 100 °C
  • 51
  • [ 863578-36-3 ]
  • C25H28N6O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; XPhos; sodium carbonate / 1,4-dioxane / 4 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 1 h / 20 °C 3: XPhos; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate / 1,4-dioxane / 2 h / 100 °C
  • 52
  • [ 863578-36-3 ]
  • C25H28N6O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; XPhos; sodium carbonate / 1,4-dioxane / 4 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 1 h / 20 °C 3: XPhos; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate / 1,4-dioxane / 2 h / 100 °C
  • 53
  • [ 863578-36-3 ]
  • C22H22N6O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; XPhos; sodium carbonate / 1,4-dioxane / 4 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 1 h / 20 °C 3: XPhos; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate / 1,4-dioxane / 2 h / 100 °C
  • 54
  • [ 863578-36-3 ]
  • C23H24N6O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; XPhos; sodium carbonate / 1,4-dioxane / 4 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 1 h / 20 °C 3: XPhos; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate / 1,4-dioxane / 2 h / 100 °C
  • 55
  • [ 863578-36-3 ]
  • C24H27N7O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; XPhos; sodium carbonate / 1,4-dioxane / 4 h / 100 °C 2: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 1 h / 20 °C 3: XPhos; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate / 1,4-dioxane / 2 h / 100 °C
  • 56
  • [ 863578-36-3 ]
  • 1-bromo-2,3-dimethoxy-5-(2-methyl-2-nitropropyl)benzene [ No CAS ]
  • 2',3'-dimethoxy-4-methyl-5'-(2-methyl-2-nitropropyl)-[1,1'-biphenyl]-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 120℃;
Same Skeleton Products
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