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[ CAS No. 5892-99-9 ] {[proInfo.proName]}

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Product Details of [ 5892-99-9 ]

CAS No. :5892-99-9 MDL No. :MFCD00463697
Formula : C11H14BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :LDUPVXSXLZOQAF-UHFFFAOYSA-N
M.W : 256.14 Pubchem ID :4498254
Synonyms :

Calculated chemistry of [ 5892-99-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.36
Num. rotatable bonds : 4
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 61.65
TPSA : 20.31 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.7
Log Po/w (XLOGP3) : 1.94
Log Po/w (WLOGP) : 2.93
Log Po/w (MLOGP) : 3.12
Log Po/w (SILICOS-IT) : 2.67
Consensus Log Po/w : 2.67

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.7
Solubility : 0.507 mg/ml ; 0.00198 mol/l
Class : Soluble
Log S (Ali) : -1.99
Solubility : 2.62 mg/ml ; 0.0102 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -4.12
Solubility : 0.0193 mg/ml ; 0.0000753 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.24

Safety of [ 5892-99-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5892-99-9 ]

* 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 [ 5892-99-9 ]

[ 5892-99-9 ] Synthesis Path-Downstream   1~100

  • 1
  • [ 109-89-7 ]
  • [ 586-75-4 ]
  • [ 5892-99-9 ]
YieldReaction ConditionsOperation in experiment
98% With triethylamine In dichloromethane at -10 - 20℃; for 0.5h; General Procedure for the Preparation of N,N-Diethyl Benzamide Precursors to Ketopyrrole Ligands, Method A: To a stirred CH2Cl2 solution (20 mL) of the benzoyl chloride at -10° C. was added triethylamine (4 mL), followed by the dropwise addition of diethylamine (1.4 equivalents). The heterogeneous reaction mixture was allowed to warm to room temperature and stirring was continued for 30 minutes. The reaction mixture was then transferred to a separatory funnel containing H2O (20 mL). The organic layer was separated and washed with 5% HCl (2*25 mL), H2O (25 ml), and dried over Na2SO4. Removal of the CH2Cl2 solvent afforded the product.
In benzene
In 1,2-dichloro-ethane at 0℃; 134.134A Oxalyl chloride (3.5 mL, 40.1 mmol) was added dropwise to a solution of 4-bromobenzoic acid (4.08 g, 20.3 mmol) and dimethyl formamide (0.04 mL) in anhydrous DCE (50 mL) at 0° C. The mixture was stirred for 2 h at rt, concentrated in vacuo and coevaporated with toluene twice. The residue was dissolved in anhydrous DCE (25 mL) and cooled in an ice bath. Diethyl amine (5 mL, 48.3 mmol) in DCE (25 mL) was added dropwise. The reaction was stirred overnight and then concentrated in vacuo. The residue was treated with 1N hydrochloric acid solution and extracted twice with dichloromethane. The organic layer was washed with water and saturated sodium chloride solution, dried (MgSO4), and concentrated in vacuo to give 134A (4.87 g, 94%) as a pink solid. LC-MS m/z: 588.19 (M+H)+.
With triethylamine In dichloromethane at 0 - 20℃;
With triethylamine Inert atmosphere;
With triethylamine In dichloromethane at 0 - 20℃;

  • 2
  • [ 78-81-9 ]
  • [ 5892-99-9 ]
  • N,N-Diethyl-4-isobutylamino-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 1,1'-bis(diphenylphosphino)ferrocene/Pd; sodium t-butanolate In tetrahydrofuran at 100℃; for 3h;
82%
  • 3
  • [ 120-72-9 ]
  • [ 5892-99-9 ]
  • N,N-Diethyl-4-indol-1-yl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; caesium carbonate In toluene at 100℃; for 12h;
  • 4
  • [ 781-35-1 ]
  • [ 5892-99-9 ]
  • N,N-Diethyl-4-(2-oxo-3,3-diphenyl-propyl)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With tol-BINAP; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In tetrahydrofuran at 70℃;
  • 5
  • [ 5892-99-9 ]
  • [ 4885-19-2 ]
YieldReaction ConditionsOperation in experiment
99% With triethyl borane; phenylsilane; sodium hydroxide In tetrahydrofuran; tert-butyl methyl ether at 20℃; Inert atmosphere; Schlenk technique; Sealed tube; chemoselective reaction;
99% With triethyl borane; phenylsilane; sodium hydroxide In tetrahydrofuran; tert-butyl methyl ether at 80℃; for 48h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;
85% With diphenylsilane In tetrahydrofuran for 20h;
  • 6
  • [ 5892-99-9 ]
  • [ 95-48-7 ]
  • N,N-diethyl-4-(2'-methylphenoxy)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; sodium hydride; johnphos 1.) toluene, 100 deg C, 15 min, 2.) toluene, 100 deg C, 22 h; Yield given; Multistep reaction;
  • 7
  • [ 4612-26-4 ]
  • [ 5892-99-9 ]
  • N,N,N',N'-tetraethyl-p-terphenyl-4,4''-dicarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; ethanol; water for 19h; Heating;
  • 8
  • [ 565-69-5 ]
  • [ 5892-99-9 ]
  • 2-(4-N,N-diethylcarbamoylphenyl)-4-methyl-3-pentanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With tris(dibenzylideneacetone)dipalladium (0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 80℃; for 24h;
  • 9
  • [ 5892-99-9 ]
  • N,N,N',N'-tetraethylbiphenyl-4,4'-dicarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: 4-bromo-N,N-diethylbenzamide With n-butyl magnesium bromide; n-butyllithium In tetrahydrofuran; hexane at -40℃; for 0.5h; Stage #2: With titanium tetrachloride In tetrahydrofuran; hexane at -40 - 0℃;
  • 10
  • [ 5892-99-9 ]
  • [ 106-95-6 ]
  • 4-allyl-N,N-diethylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% Stage #1: 4-bromo-N,N-diethylbenzamide With lithium dibutyl(isopropyl)magnesate In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: allyl bromide In tetrahydrofuran; hexane at -78℃; for 1h;
  • 11
  • [ 5720-07-0 ]
  • [ 5892-99-9 ]
  • [ 331816-27-4 ]
YieldReaction ConditionsOperation in experiment
99% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In methanol; benzene at 80℃; for 17h;
99% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In methanol; water; benzene at 80℃; for 17h;
  • 12
  • [ 5892-99-9 ]
  • [ 123-38-6 ]
  • lithium dibutyl(isopropyl)magnesate [ No CAS ]
  • N,N-diethyl-4-(1-hydroxypropyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% Stage #1: 4-bromo-N,N-diethylbenzamide; lithium dibutyl(isopropyl)magnesate In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: propionaldehyde In tetrahydrofuran; hexane at -78℃; Further stages.;
  • 13
  • [ 5892-99-9 ]
  • [ 106-95-6 ]
  • lithium dibutyl(isopropyl)magnesate [ No CAS ]
  • 4-allyl-N,N-diethylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% Stage #1: 4-bromo-N,N-diethylbenzamide; lithium dibutyl(isopropyl)magnesate In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: allyl bromide With CuCN*2LiCl In tetrahydrofuran; hexane at -78℃; Further stages.;
  • 14
  • [ 5892-99-9 ]
  • [ 51207-85-3 ]
YieldReaction ConditionsOperation in experiment
99% With tris(dibenzylideneacetone)dipalladium (0); lithium hexamethyldisilazane; CyJohnPhos In 1,4-dioxane at 80℃; for 15h;
94% With dicyclohexyl(2',4',6'-triisopropyl-5-methoxy-3,4,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; C50H70NO4PPdS; C50H70NO4PPdS; dicyclohexyl(2',4',6'-triisopropyl-4-methoxy-3,5,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 20℃; for 36h; Inert atmosphere;
  • 15
  • [ 5892-99-9 ]
  • [ 101-97-3 ]
  • ethyl α-phenyl-α-(4-N,N-diethylcarbamoylphenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With palladium diacetate; lithium hexamethyldisilazane; DavePhos In toluene at 80℃; for 1h;
  • 16
  • [ 5892-99-9 ]
  • [ 331816-28-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 99 percent / Pd(PPh3)4; 2M aq. Na2CO3 / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating
Multi-step reaction with 3 steps 1.1: 99 percent / Na2CO3; Pd(PPh3)4 / benzene; methanol; H2O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C
  • 17
  • [ 5892-99-9 ]
  • 3-(3-benzyl-4'-methoxy-biphenyl-4-yl)-propionyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 99 percent / Pd(PPh3)4; 2M aq. Na2CO3 / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH2Cl2; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C 5.1: 94 percent / H2 / 10 percent Pd/C / ethanol / 36 h / 20 °C 6.1: SOCl2 / CH2Cl2 / 3 h / 60 °C
Multi-step reaction with 7 steps 1.1: 99 percent / Na2CO3; Pd(PPh3)4 / benzene; methanol; H2O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH2Cl2 / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H2 / Pd/C / ethanol / 36 h / 20 °C 7.1: SOCl2 / CH2Cl2 / 3 h / 60 °C
  • 18
  • [ 5892-99-9 ]
  • [ 395681-97-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 99 percent / Pd(PPh3)4; 2M aq. Na2CO3 / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH2Cl2; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C 5.1: 94 percent / H2 / 10 percent Pd/C / ethanol / 36 h / 20 °C
Multi-step reaction with 6 steps 1.1: 99 percent / Na2CO3; Pd(PPh3)4 / benzene; methanol; H2O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH2Cl2 / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H2 / Pd/C / ethanol / 36 h / 20 °C
  • 19
  • [ 5892-99-9 ]
  • [ 331816-30-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: 99 percent / Pd(PPh3)4; 2M aq. Na2CO3 / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH2Cl2; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C 5.1: 94 percent / H2 / 10 percent Pd/C / ethanol / 36 h / 20 °C 6.1: SOCl2 / CH2Cl2 / 3 h / 60 °C 7.1: TiCl4 / CH2Cl2 / 12 h / 0 - 5 °C
Multi-step reaction with 8 steps 1.1: 99 percent / Na2CO3; Pd(PPh3)4 / benzene; methanol; H2O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH2Cl2 / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H2 / Pd/C / ethanol / 36 h / 20 °C 7.1: SOCl2 / CH2Cl2 / 3 h / 60 °C 8.1: 85 mg / TiCl4 / CH2Cl2 / 12 h / 0 - 5 °C
  • 20
  • [ 5892-99-9 ]
  • [ 391864-70-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 99 percent / Pd(PPh3)4; 2M aq. Na2CO3 / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH2Cl2; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C
Multi-step reaction with 5 steps 1.1: 99 percent / Na2CO3; Pd(PPh3)4 / benzene; methanol; H2O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH2Cl2 / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C
  • 21
  • [ 5892-99-9 ]
  • [ 331816-32-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: 99 percent / Pd(PPh3)4; 2M aq. Na2CO3 / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH2Cl2; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C 5.1: 94 percent / H2 / 10 percent Pd/C / ethanol / 36 h / 20 °C 6.1: SOCl2 / CH2Cl2 / 3 h / 60 °C 7.1: TiCl4 / CH2Cl2 / 12 h / 0 - 5 °C 8.1: 74 percent / 2.5M aq. NaOH / ethanol / 24 h / 20 °C 9.1: 70 percent / H2 / Pt2O / ethanol; ethyl acetate / 15 h / 20 °C
Multi-step reaction with 10 steps 1.1: 99 percent / Na2CO3; Pd(PPh3)4 / benzene; methanol; H2O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH2Cl2 / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H2 / Pd/C / ethanol / 36 h / 20 °C 7.1: SOCl2 / CH2Cl2 / 3 h / 60 °C 8.1: 85 mg / TiCl4 / CH2Cl2 / 12 h / 0 - 5 °C 9.1: 74 percent / NaOH / ethanol; H2O / 24 h / 20 °C 10.1: 70 percent / H2 / PtO2 / ethanol; ethyl acetate / 15 h / 20 °C
  • 22
  • [ 5892-99-9 ]
  • 4-benzyl-2-(4-hydroxy-benzyl)-6-(4-hydroxy-phenyl)-indan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: 99 percent / Pd(PPh3)4; 2M aq. Na2CO3 / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH2Cl2; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C 5.1: 94 percent / H2 / 10 percent Pd/C / ethanol / 36 h / 20 °C 6.1: SOCl2 / CH2Cl2 / 3 h / 60 °C 7.1: TiCl4 / CH2Cl2 / 12 h / 0 - 5 °C 8.1: 74 percent / 2.5M aq. NaOH / ethanol / 24 h / 20 °C 9.1: 70 percent / H2 / Pt2O / ethanol; ethyl acetate / 15 h / 20 °C 10.1: 52 percent / BBr3 / CH2Cl2 / 53 h / -78 - 20 °C
Multi-step reaction with 11 steps 1.1: 99 percent / Na2CO3; Pd(PPh3)4 / benzene; methanol; H2O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH2Cl2 / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H2 / Pd/C / ethanol / 36 h / 20 °C 7.1: SOCl2 / CH2Cl2 / 3 h / 60 °C 8.1: 85 mg / TiCl4 / CH2Cl2 / 12 h / 0 - 5 °C 9.1: 74 percent / NaOH / ethanol; H2O / 24 h / 20 °C 10.1: 70 percent / H2 / PtO2 / ethanol; ethyl acetate / 15 h / 20 °C 11.1: 52 percent / BBr3 / CH2Cl2 / 53 h / -78 - 20 °C
  • 23
  • [ 5892-99-9 ]
  • (S)-4-benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)-indan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1.1: 99 percent / Pd(PPh3)4; 2M aq. Na2CO3 / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH2Cl2; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C 5.1: 94 percent / H2 / 10 percent Pd/C / ethanol / 36 h / 20 °C 6.1: SOCl2 / CH2Cl2 / 3 h / 60 °C 7.1: TiCl4 / CH2Cl2 / 12 h / 0 - 5 °C 8.1: 74 percent / 2.5M aq. NaOH / ethanol / 24 h / 20 °C 9.1: 70 percent / H2 / Pt2O / ethanol; ethyl acetate / 15 h / 20 °C 10.1: 52 percent / BBr3 / CH2Cl2 / 53 h / -78 - 20 °C 11.1: HPLC DIACEL OC column / hexane; ethanol
Multi-step reaction with 12 steps 1.1: 99 percent / Na2CO3; Pd(PPh3)4 / benzene; methanol; H2O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH2Cl2 / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H2 / Pd/C / ethanol / 36 h / 20 °C 7.1: SOCl2 / CH2Cl2 / 3 h / 60 °C 8.1: 85 mg / TiCl4 / CH2Cl2 / 12 h / 0 - 5 °C 9.1: 74 percent / NaOH / ethanol; H2O / 24 h / 20 °C 10.1: 70 percent / H2 / PtO2 / ethanol; ethyl acetate / 15 h / 20 °C 11.1: 52 percent / BBr3 / CH2Cl2 / 53 h / -78 - 20 °C 12.1: chiral HPLC
  • 24
  • [ 5892-99-9 ]
  • (R)-4-benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)-indan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1.1: 99 percent / Pd(PPh3)4; 2M aq. Na2CO3 / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH2Cl2; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C 5.1: 94 percent / H2 / 10 percent Pd/C / ethanol / 36 h / 20 °C 6.1: SOCl2 / CH2Cl2 / 3 h / 60 °C 7.1: TiCl4 / CH2Cl2 / 12 h / 0 - 5 °C 8.1: 74 percent / 2.5M aq. NaOH / ethanol / 24 h / 20 °C 9.1: 70 percent / H2 / Pt2O / ethanol; ethyl acetate / 15 h / 20 °C 10.1: 52 percent / BBr3 / CH2Cl2 / 53 h / -78 - 20 °C 11.1: HPLC DIACEL OC column / hexane; ethanol
Multi-step reaction with 12 steps 1.1: 99 percent / Na2CO3; Pd(PPh3)4 / benzene; methanol; H2O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH2Cl2 / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H2 / Pd/C / ethanol / 36 h / 20 °C 7.1: SOCl2 / CH2Cl2 / 3 h / 60 °C 8.1: 85 mg / TiCl4 / CH2Cl2 / 12 h / 0 - 5 °C 9.1: 74 percent / NaOH / ethanol; H2O / 24 h / 20 °C 10.1: 70 percent / H2 / PtO2 / ethanol; ethyl acetate / 15 h / 20 °C 11.1: 52 percent / BBr3 / CH2Cl2 / 53 h / -78 - 20 °C 12.1: chiral HPLC
  • 25
  • [ 5892-99-9 ]
  • [ 391864-73-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: 99 percent / Pd(PPh3)4; 2M aq. Na2CO3 / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH2Cl2; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C 5.1: 94 percent / H2 / 10 percent Pd/C / ethanol / 36 h / 20 °C 6.1: SOCl2 / CH2Cl2 / 3 h / 60 °C 7.1: TiCl4 / CH2Cl2 / 12 h / 0 - 5 °C 8.1: 74 percent / 2.5M aq. NaOH / ethanol / 24 h / 20 °C
Multi-step reaction with 9 steps 1.1: 99 percent / Na2CO3; Pd(PPh3)4 / benzene; methanol; H2O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH2Cl2 / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H2 / Pd/C / ethanol / 36 h / 20 °C 7.1: SOCl2 / CH2Cl2 / 3 h / 60 °C 8.1: 85 mg / TiCl4 / CH2Cl2 / 12 h / 0 - 5 °C 9.1: 74 percent / NaOH / ethanol; H2O / 24 h / 20 °C
  • 26
  • [ 5892-99-9 ]
  • (R)-4-benzyl-2-(4-hydroxybenzyl)-2-hydroxymethyl-6-(4-hydroxyphenyl)-indan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1.1: 99 percent / Pd(PPh3)4; 2M aq. Na2CO3 / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH2Cl2; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C 5.1: 94 percent / H2 / 10 percent Pd/C / ethanol / 36 h / 20 °C 6.1: SOCl2 / CH2Cl2 / 3 h / 60 °C 7.1: TiCl4 / CH2Cl2 / 12 h / 0 - 5 °C 8.1: 74 percent / 2.5M aq. NaOH / ethanol / 24 h / 20 °C 9.1: 70 percent / H2 / Pt2O / ethanol; ethyl acetate / 15 h / 20 °C 10.1: 52 percent / BBr3 / CH2Cl2 / 53 h / -78 - 20 °C 11.1: 60 percent / 2.5M aq. NaOH / ethanol / 2 h / 20 °C 12.1: HPLC DIACEL OC column / hexane; ethanol
Multi-step reaction with 13 steps 1.1: 99 percent / Na2CO3; Pd(PPh3)4 / benzene; methanol; H2O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH2Cl2 / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H2 / Pd/C / ethanol / 36 h / 20 °C 7.1: SOCl2 / CH2Cl2 / 3 h / 60 °C 8.1: 85 mg / TiCl4 / CH2Cl2 / 12 h / 0 - 5 °C 9.1: 74 percent / NaOH / ethanol; H2O / 24 h / 20 °C 10.1: 70 percent / H2 / PtO2 / ethanol; ethyl acetate / 15 h / 20 °C 11.1: 52 percent / BBr3 / CH2Cl2 / 53 h / -78 - 20 °C 12.1: NaOH / ethanol; H2O / 2 h / 20 °C 13.1: chiral HPLC
  • 27
  • [ 5892-99-9 ]
  • (S)-4-benzyl-2-(4-hydroxybenzyl)-2-hydroxymethyl-6-(4-hydroxyphenyl)-indan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1.1: 99 percent / Pd(PPh3)4; 2M aq. Na2CO3 / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH2Cl2; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C 5.1: 94 percent / H2 / 10 percent Pd/C / ethanol / 36 h / 20 °C 6.1: SOCl2 / CH2Cl2 / 3 h / 60 °C 7.1: TiCl4 / CH2Cl2 / 12 h / 0 - 5 °C 8.1: 74 percent / 2.5M aq. NaOH / ethanol / 24 h / 20 °C 9.1: 70 percent / H2 / Pt2O / ethanol; ethyl acetate / 15 h / 20 °C 10.1: 52 percent / BBr3 / CH2Cl2 / 53 h / -78 - 20 °C 11.1: 60 percent / 2.5M aq. NaOH / ethanol / 2 h / 20 °C 12.1: HPLC DIACEL OC column / hexane; ethanol
Multi-step reaction with 13 steps 1.1: 99 percent / Na2CO3; Pd(PPh3)4 / benzene; methanol; H2O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH2Cl2 / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H2 / Pd/C / ethanol / 36 h / 20 °C 7.1: SOCl2 / CH2Cl2 / 3 h / 60 °C 8.1: 85 mg / TiCl4 / CH2Cl2 / 12 h / 0 - 5 °C 9.1: 74 percent / NaOH / ethanol; H2O / 24 h / 20 °C 10.1: 70 percent / H2 / PtO2 / ethanol; ethyl acetate / 15 h / 20 °C 11.1: 52 percent / BBr3 / CH2Cl2 / 53 h / -78 - 20 °C 12.1: NaOH / ethanol; H2O / 2 h / 20 °C 13.1: chiral HPLC
  • 28
  • [ 5892-99-9 ]
  • [ 331816-33-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 99 percent / Pd(PPh3)4; 2M aq. Na2CO3 / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH2Cl2; hexane / 0.5 h / -78 °C
Multi-step reaction with 4 steps 1.1: 99 percent / Na2CO3; Pd(PPh3)4 / benzene; methanol; H2O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH2Cl2 / 0.5 h / -78 °C
  • 29
  • [ 5892-99-9 ]
  • [ 331816-26-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1.1: 99 percent / Pd(PPh3)4; 2M aq. Na2CO3 / benzene; methanol / 17 h / 80 °C 2.1: TMEDA; sec-BuLi / tetrahydrofuran / 1.17 h / -78 °C 2.2: 80 percent / toluene / 12 h / Heating 3.1: 90 percent / DIBAL / CH2Cl2; hexane / 0.5 h / -78 °C 4.1: 95 percent / benzene / 1 h / 80 °C 5.1: 94 percent / H2 / 10 percent Pd/C / ethanol / 36 h / 20 °C 6.1: SOCl2 / CH2Cl2 / 3 h / 60 °C 7.1: TiCl4 / CH2Cl2 / 12 h / 0 - 5 °C 8.1: 74 percent / 2.5M aq. NaOH / ethanol / 24 h / 20 °C 9.1: 70 percent / H2 / Pt2O / ethanol; ethyl acetate / 15 h / 20 °C 10.1: 52 percent / BBr3 / CH2Cl2 / 53 h / -78 - 20 °C 11.1: 60 percent / 2.5M aq. NaOH / ethanol / 2 h / 20 °C
Multi-step reaction with 12 steps 1.1: 99 percent / Na2CO3; Pd(PPh3)4 / benzene; methanol; H2O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH2Cl2 / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H2 / Pd/C / ethanol / 36 h / 20 °C 7.1: SOCl2 / CH2Cl2 / 3 h / 60 °C 8.1: 85 mg / TiCl4 / CH2Cl2 / 12 h / 0 - 5 °C 9.1: 74 percent / NaOH / ethanol; H2O / 24 h / 20 °C 10.1: 70 percent / H2 / PtO2 / ethanol; ethyl acetate / 15 h / 20 °C 11.1: 52 percent / BBr3 / CH2Cl2 / 53 h / -78 - 20 °C 12.1: NaOH / ethanol; H2O / 2 h / 20 °C
  • 30
  • [ 5892-99-9 ]
  • 3-(hydroxy-phenyl-methyl)-4'-methoxy-biphenyl-4-carboxylic acid diethylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 99 percent / Na2CO3; Pd(PPh3)4 / benzene; methanol; H2O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C
  • 31
  • [ 5892-99-9 ]
  • 4-Benzyl-6-(4-hydroxy-phenyl)-2-[1-(4-hydroxy-phenyl)-meth-(E)-ylidene]-indan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: 99 percent / Na2CO3; Pd(PPh3)4 / benzene; methanol; H2O / 17 h / 80 °C 2.1: sec-BuLi; TMEDA / tetrahydrofuran / 0.83 h / -78 °C 2.2: 1.0 g / tetrahydrofuran / 0.5 h / -78 °C 3.1: 900 mg / toluene / 12 h / 110 °C 4.1: 90 percent / DIBAL / CH2Cl2 / 0.5 h / -78 °C 5.1: 95 percent / benzene / 1 h / 80 °C 6.1: 94 percent / H2 / Pd/C / ethanol / 36 h / 20 °C 7.1: SOCl2 / CH2Cl2 / 3 h / 60 °C 8.1: 85 mg / TiCl4 / CH2Cl2 / 12 h / 0 - 5 °C 9.1: 74 percent / NaOH / ethanol; H2O / 24 h / 20 °C 10.1: 50 percent / BBr3 / CH2Cl2 / 29 h / -78 - 20 °C
  • 32
  • [ 5892-99-9 ]
  • [ 255850-51-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diethylamine; CuI; (PPh3)4Pd / 11 h / Heating 2: 0.65 g / potassium hydroxide / toluene / 1 h / Heating
  • 33
  • [ 5892-99-9 ]
  • p-(4-(p-diethylcarbamoylphenyl)-1,3-butadiynyl)-N,N-diethylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diethylamine; CuI; (PPh3)4Pd / 11 h / Heating 2: 0.65 g / potassium hydroxide / toluene / 1 h / Heating 3: 53 percent / tetramethylethylenediamine; CuCl; oxygen / acetone / 20 h
  • 34
  • [ 5892-99-9 ]
  • [ 6238-20-6 ]
  • [ 682777-61-3 ]
YieldReaction ConditionsOperation in experiment
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100 - 150℃; for 16h; 1 Example 1; [N, N-DIETHYL-4- [PHENYL- (1-AZABICYCLO] [2.2. 2] octan-3-amino) ] benzamide Fumarate [1: 1]; (Compound 1) (Method [1A)] To a mixture of 9.3 g (0.1 mol) of aniline and 16.1 g (0.1 mol) of 1-azabicyclo [2.2. 2] octan-3-one hydrochloride in 250 mL of dichloroethane (DCE) was added 31.8 g (0.15 mol) of Na [(OAC)] 3BH and the mixture was stirred overnight at room temperature. The reaction was quenched with 3 N [NAOH.] The layers were separated and the aqueous layer was extracted with an additional portion of CHCi3. The organic layers were combined, dried over [NAS04,] and then filtered and the solvent was evaporated in vacuo. The residue was chromatographed on silica (95/5 [CHCI3/10] % NH40H in MeOH) to give [N-PHENYL-1-AZABICYCLO] [2.2. 2] [OCTAN-3-AMINE] (6.0 g 30 %) as an off-white solid. MH+ = [203.'H] NMR [(CDCI3)] 1.46 (m, [1 H),] 1.75 (m, [3H),] 2.0 (m, 1 H), 2.55 (m, 1 H), 2.95 (m, 4H), 3.4 (m, [2H),] 3.8 (s, 1 H), 6.6 (d, [2H),] [6.] 75 (t, 1H), 7.2 (t, [2H).] (Method 1 B) A mixture of 1.26 g of 1-azabicyclo [2.2. 2] octan-3-one and 0.93 g of aniline and 4.4 mL of Ti [(/PRO)] 4 was stirred overnight at room temperature. The reaction mixture was diluted with [ETOH] and then NaBH4 pellets (0.8 g) were added until reaction was judged complete by TLC. The solvent was evaporated in vacuo. The residue was diluted with 3N [NAOH,] water and EtOAc and the mixture was filtered through dicalite. The filter pad was washed with additional EtOAc. The filtrate was transferred to a separatory funnel and the aqueous layer was extracted with an additional portion of EtOAc. The combined organic extracts were washed with water and then brine and then dried over [K2CO3.] The solution was filtered and the solvent was evaporated in vacuo. The residue was chromatographed on silica [(90/7.] [5/2.] 5 [CHCI3/MEOH/7.] 0 M [NH3] in [MEOH)] to give N-Phenyl-1-azabicyclo [2.2. 2] [OCTAN-3-AMINE] (1.5 g, 75 %) as a white [SOLID.'H] NMR [(CDC13)] is consistent with the one from Method 1A. A solution of 0.5 g (2.5 [MMOL)] of [N-PHENYL-1-AZABICYCLO] [2.2. 2] octan-3-amine, 0.64 g (2.5 [MMOL)] of [NN-DIETHYL-4-BROMOBENZAMIDE,] 23 mg (0.025 [MMOL)] of tris [(DIBENZYLIDENEACETONE)-DIPALLADIUM (0)] (Pd2 (dba) 3), and 47 mg (0.075 [MMOL)] of BINAP and 0.36 g (3.75 [MMOL)] of NaOtBu in 5 mL of dry toluene was heated at 100-150° C for 16 hrs. The reaction mixture was cooled and diluted with water and EtOAc. The aqueous layer was extracted with a second portion of EtOAc and the combined extracts were washed with water and then with brine and then dried over [K2C03.] The solution was filtered and the solvent was evaporated in vacuo. The residue was chromatographed on silica (96/4 CHCl3/10% NH40H in [MEOH).] The appropriate fractions were combined and the solvent was evaporated in vacuo. The residue was combined with 1 eq. of fumaric acid in [2-PROH.'THE SOLVENT] was evaporated in vacuo and the residue recrystallized from acetone to give Compound 1 (0.45 [G,] 37%) as a white solid mp 181-183°C. MH+ = 378. 1H NMR [(DMSO-D6)] 1.05 (t, 6H), 1.35 (m, [1H),] 1.65 (m, [1H),] 1.8 [(M,] [2H),] 2.05 (br s, 1H). 2.7 (m, [1 H),] 3.0 (m, 4H), 3.3 (br s, 4H), 3.55 (t, [1H),] 4.3 (t, [1H),] 6.45 (s, 2H), 6.8 (d, 2H), 7. 2 (m, [5H),] 7.4 (t, 2H). Anal. Calcd for [C24H3N3O C4H404] : C, 68.13 ; H, 7.15 ; N, 8.51. Found C, 67.81 ; H, 7.03 ; [N,] 8.40.
  • 35
  • [ 109-89-7 ]
  • [ 589-17-3 ]
  • [ 5892-99-9 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane i I. (i) Preparation of 4-bromo-N,N-diethyl Benzamide (Compound 1). To an ice cooled solution of 4-bromobenzyl chloride (19.5 g, 86.8 mmol) in 150 ml of CH2Cl2 was added dropwise (13.5 ml, 130 mmol) of diethylamine. The reaction is stirred overnight then concentrated. The mixture is taken into ether and 1 HCl and the aqueous layer separated. The organic layer was extracted a further two times with ether then washed with brine and dried over Na2SO4. The resulting oil was taken into ethyl acetate and allowed to crystallize. 2 more crystallizations of the mother liquor yielded 18.6 g, 83.6%.
  • 36
  • [ 229479-46-3 ]
  • CH2Cl2:MeOH [ No CAS ]
  • [ 5892-99-9 ]
  • N,N-diethyl-4-[3-methoxyphenyl(1-propylpiperidin-4-yl)amino]benzamide [ No CAS ]
  • [ 229479-39-4 ]
YieldReaction ConditionsOperation in experiment
53% With ammonium hydroxide In toluene 1 N,N-Diethyl-4-[3-methoxyphenyl(1-propylpiperidin-4-yl)amino]benzamide Fumarate [1:1], C1 Example 1 N,N-Diethyl-4-[3-methoxyphenyl(1-propylpiperidin-4-yl)amino]benzamide Fumarate [1:1], C1 A solution of 3.5 g (14.1 mmol) of N-(3-methoxyphenyl)-1-propyl-4-piperidinamine, 3.61 g (14.1 mmol) of N,N-diethyl-4-bromobenzamide, 129 mg (0.141 mmol) tris(dibenzylideneacetone)-dipalladium(0) (Pd2dba3), 263 mg (0.423 mmol) of (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binapthyl (+BINAP) and 1.89 g (19.7 mmol) of sodium t-butoxide in 25 mL of dry toluene was heated at 110° C. under Ar in a pressure vessel for 16 h. The mixture was cooled and partitioned between CH2Cl2 and H2O. The organic layer was washed with brine, dried (K2CO3) and the solvent was evaporated. The residue was chromatographed on a Biotage Flash 75 unit using CH2Cl2:MeOH:NH4OH, 92:8:0.8 as eluent. There was obtained 3.2 g (53% yield) of N,N-diethyl-4-[3-methoxyphenyl(1-propylpiperidin-4yl)amino]benzamide as a solid. A fumarate salt was prepared out of 2-PrOH: mp 168-169° C. MS m/z=424 (M++H). 300 MHz 1H NMR (DMSO-d6) δ7.3 (t, 1H); 7.2 (d, 2H); 6.8 (d, 1H); 6.6 (m, 4H); 6.5 (s, 2H); 4.0 (m, 1H); 3.75 (s, 3H); 3.3 (q, 4H); 3.1 (d, 2H); 2.4 (m, 4H); 1.9 (d, 2H); 1.4 (m, 4H); 1.1 (t, 6H); 0.8 (t, 3H). Anal calcd. for C26H37N3O2.C4H4O4: C, 66.77; H, 7.65; N, 7.78. Found: C, 66.69; H, 7.76; N 7.68.
  • 37
  • [ 584-08-7 ]
  • [ 5892-99-9 ]
  • [ 588-16-9 ]
  • N,N-diethyl-4-[N-(3-methoxyphenyl)amino]benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With CuI In dichloromethane; water 1 N,N-Diethyl-4-[N-(3-methoxyphenyl)amino]benzamide PREPARATION 1 N,N-Diethyl-4-[N-(3-methoxyphenyl)amino]benzamide 3.7 g (2.3 mmol) of N-acetyl-m-anisidine, 10.6 g (41.4 mmol) of 4-bromo-N,N-diethylbenzamide and 0.42 g of CuI were heated to 1000° C.; 3 g (22.3 mmol) of K2 CO3 were added and the resulting mixture was heated to 250° C. for 2 hours. The residue was dissolved in CH2 Cl2 and washed with H2 O, the organic layer was dried over Na2 SO4 and the solvent was removed in vacuo. The resulting residue was dissolved in 20 ml of absolute EtOH and refluxed for 2 h. The solvent was removed in vacuo, the residue was taken up in H2 O and the aqueous layer extracted with AcOEt. The organic layer was dried over Na2 SO4 and the solvent removed in vacuo. The resulting residue was purified by flash chromatography (AcOEt/Hexane 6:4), yielding 3 g of the title compound. IR cm- (neat): 3300, 1595, 1535. MS (EI) m/z: 297.6 (M-1)
  • 38
  • PD2 [ No CAS ]
  • [ 5892-99-9 ]
  • [ 206273-87-2 ]
  • N,N-diethyl-4-[phenyl(1-(tert-butoxycarbonyl)piperidin-4-yl)amino]benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; water; toluene 4 N,N-Diethyl-4-[benzyl(piperidin-4-yl)amino]benzamide (Compound 8) A solution of 4-benzylamino-1-(tert-butoxycarbonyl)piperidine (2.63 g, 9.06 mmol), N,N-diethyl-4-bromobenzamide (2.32 g, 9.06 mmol), Pd2 dba3 (0.08 g, 0.091 mmol), (+)-BINAP (0.17 g, 0.272 mmol) and sodium t-butoxide (1.22 g, 12.7 mmol) in 18 mL of dry toluene was heated at 120° C. under Argon in a pressure vessel for 48 h. The mixture was cooled, and dichloromethane (75 mL) and water (75 mL) were added to the reaction flask. The layers were separated, and the aqueous layer was extracted twice with dichloromethane (75 mL). The organic layers were combined and washed with brine (75 mL) and dried (Na2SO4). Evaporation of the solvent afforded a dark brown semi-solid. This material was purified on a flash silica gel column (5% methanol-chloroform) to provide 2.79 g of impure product. This material was repurified on a flash silica gel column (5% methanol-chloroform) to give 1.11 g of N,N-diethyl-4-[phenyl(1-(tert-butoxycarbonyl)piperidin-4-yl)amino]benzamide as a golden-brown semisolid. MS (ES), m/z 466 (MH+). 300 MHz 1H NMR (CDCl3) δ1.02-1.33 (br m, 6H), 1.17 (t, J=7.0 Hz, 3H), 1.45 (s, 9H), 11.50-1.69 (br q, 2H), 1.85 (br d, J=12.1 Hz, 2H), 2.81 (br t, J=12.3 Hz, 2H), 3.16-3.34 (br m, 2H), 3.32-3.48 (br q, 2H), 3.47-3.62 (br m, 2H), 3.88-4.02 (br m, 1H), 4.02-4.38 (br m, 2H), 4.48 (br s, 2H), 6.67 (d, J=8.8 Hz, 2H), 7.14-7.29 (m, 4H), 7.32-7.40 (m, 3H).
  • 39
  • (8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-(3-methoxy-phenyl)-methanone [ No CAS ]
  • [ 5892-99-9 ]
  • 4-[(8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-hydroxy-(3-methoxy-phenyl)-methyl]-N,N-diethyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-bromo-N,N-diethylbenzamide With n-butyllithium In tetrahydrofuran; hexanes at -100 - -90℃; for 0.25h; Stage #2: (8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-(3-methoxy-phenyl)-methanone In tetrahydrofuran; hexanes at -78 - 20℃; for 4h; 3 EXAMPLE 3 4-R (8-BENZVL-8-AZA-BICVCLOF3. 2. 1 (3-METHOXV-PHENYL)-METHVLL-N, N- DIETHVL-BENZAMIDE. To a solution of 4-bromo-N, N-diethyl-benzamide (3.16g) in THF (20 mL) at-100 C was added n-BuLi (2.5M in hexanes, 4.9 mL) slowly so the internal temperature would not rise above-90 C. The mixture was stirred at-100 C for 15 minutes. To the reaction was added a solution of ketone 3 (2.75 g) in THF (10 mL) in one portion. The reaction mixture was stirred at-78 C for 1 hour and then was warmed to room temperature over the course of 3 hours. The mixture was poured into a saturated aqueous solution of sodium bicarbonate (30 mL). The aqueous layer was washed with EtOAc (3x 30 mL) and the combined organic extracts were dried over magnesium sulfate and concentrated under vacuum. Purification by flash chromatography with methanol/EtOAc (1: 10) afforded alcohol 12 (2.1 g).'HNMR (400 MHz, CDCI3) 8 6.65 (d, 1 H), 3.21 (s, 2H), 2.94-2. 81 (m, 1 H); MS (M+1) = 513
  • 42
  • [ 477178-66-8 ]
  • [ 5892-99-9 ]
  • [ 477178-67-9 ]
YieldReaction ConditionsOperation in experiment
79% With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 110℃;
  • 43
  • [ 50541-93-0 ]
  • [ 5892-99-9 ]
  • [ 209902-02-3 ]
YieldReaction ConditionsOperation in experiment
77% With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 80℃;
  • 44
  • [ 5892-99-9 ]
  • [ 1122-91-4 ]
YieldReaction ConditionsOperation in experiment
96% With zirconocene dichloride; lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at 20℃; for 0.0333333h; 1a Synthesis of 4-Bromobenzaldehyde Using the In Situ Schwartz Reagent Method To a solution of N,N-diethyl-4-bromo-benzamide (128 mg, 0.5 mmol) (see structural formula at entry 3 of Table 1) and Cp2ZrCl2(207 mg, 0.7 mmol, 1.4 eq.) in THF (3 mL) at RT was rapidly added a 1 M tetrahydrofuran (THF) solution of LiAlH(Ot-Bu)3 (0.7 mL, 0.7 mmol, 1.4 eq.). After addition, thin layer chromatography (TLC) using EtOAc/Hexanes showed the substrate had been consumed completely. The reaction was quenched by distilled H2O immediately. Dilute acid (0.5 N HCl in distilled water) was added until the pH was less than 5. Then EtOAc was added (3×10 mL) and the mixture was extracted. Combined organic layers were washed with brine, dried over MgSO4 and concentrated via evaporation under reduced pressure. Initial purification of the crude product was performed by passing the solution through a filter of silica gel (silica gel 60, 230-400 mesh). Purity was then checked by TLC. If further purification was needed, it was performed by flash column chromatography (silica gel 60, 230-400 mesh) using EtOAc/hexanes as eluent. 4-Bromobenzaldehyde (89 mg, 96% yield) was obtained as a colorless solid. Its melting point was determined to be 55-56° C. (hexanes).1H NMR (400 MHz, CDCl3) δ ppm: 9.98 (s, 1H), 7.75 (d, J=8.31 Hz, 2H), 7.69 (d, J=8.37 Hz, 2H).13C NMR (101 MHz, CDCl3) δ ppm: 191.02, 135.05, 132.42, 130.94, 129.76.The physical and spectral data were consistent with those reported by Lee et al. (see Lee, K.; Maleczka, R. E., Org. Lett. 2006, 8, 1887-1888), who reported a melting point of 54-56° C.
96% With zirconocene dichloride; lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at 20℃; for 0.0333333h; Inert atmosphere;
  • 45
  • [ 5892-99-9 ]
  • [ 4294-57-9 ]
  • N,N-diethyl-4′-methylbiphenyl-4-carboxamide [ No CAS ]
  • [ 613-33-2 ]
  • 46
  • [ 5892-99-9 ]
  • [ 33513-42-7 ]
  • [ 918811-37-7 ]
YieldReaction ConditionsOperation in experiment
45% Stage #1: With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.25h; Stage #2: 4-bromo-N,N-diethylbenzamide In tetrahydrofuran; hexane at -78℃; for 1h; Stage #3: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78 - 20℃; for 0.833333h; 134.134B An oven dried round bottom flask was charged with anhydrous THF (20 mL) and 2,2,6,6-tetramethyl piperidine (0.68 mL, 4.0 mmol). The mixture was cooled in an ice bath and 1.46 M n-butyl lithium in hexane (2.8 mL, 4.09 mmol) was added dropwise over 5 min. After 10 min, the solution was cooled to -78° C. and a solution of 134A (512 mg, 2.0 mmol) in anhydrous THF (2 mL) was added quickly down the side of flask to precool the solution. After 1 h at -78° C. dimethyl formamide (0.5 mL, 6.38 mmol) was added dropwise and the mixture was stirred at -78° C. for 20 min and at RT for 30 min. Water was added dropwise followed by ethyl acetate. The mixture was extracted twice with ethyl acetate. The organic layer was washed with water, saturated sodium chloride solution, dried (MgSO4) and concentrated in vacuo to give 134B (0.256 g, 45%) as yellow oil. LC-MS m/z: 286.16 (M+H)+.
  • 47
  • [ 99-61-6 ]
  • [ 5892-99-9 ]
  • [ 691877-61-9 ]
YieldReaction ConditionsOperation in experiment
67% Stage #1: With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane at -10 - -5℃; for 1.5h; Inert atmosphere; Stage #2: 3-nitro-benzaldehyde; 4-bromo-N,N-diethylbenzamide With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran; hexane at -40 - -20℃; Stage #3: With hydrogenchloride; sodium hydroxide In tetrahydrofuran; hexane; water n-BuLi (234 mL, 2.5 M solution in hexanes, 585 mmol) was added to a solution of THF (300 mL) and n-BuMgCl (146 mL, 292 mmol, 2M in THF) at -10 to -5 °C over a period of 60 min and the resulting solution was stirred for a further 30 min. The resulting solution was cooled to -40 °C. A solution of N,N-diethyl-4-bromobenzamide (150 g, 586 mmol) in THF (150 mL) was then added over 90 min, and following complete addition the reaction mixture was held for 30 min before being warmed to -25 to -20 °C. l,3-dimethyl-3,4,5,6-tetrahydro- 2(lH)-pyrimidinone (150 mL) was added, followed the addition of a solution of 3- nitrobenzaldehyde (79.7 g, 527 mmol) in THF (150 mL) over at least 60 min. The reaction was held for 60 min before concentrated HC1 (103 g of 36-38% w/w) in water (131 mL) was added and the reaction was allowed to warm to room temperature. The lower aqueous phase was discarded and the organic layer was washed with aqueous NaHC03 (7.1 g in 150 mL), followed by water (150 mL). The residue was purified by flash chromatography on silica gel eluting with toluene and then butyl acetate to provide Compound 2 (129.5 g, 67%).Analysis: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.06 (m, 6 H) 3.16 (m, 2 H) 3.39 (m, 2 H) 5.91 (d, J=4.2 Hz, 1 H) 6.30 (d, J=4.2 Hz, 1 H) 7.29 (d, J=8.2 Hz, 2 H) 7.45 (d, J=8.2 Hz, 2 H) 7.61 (t, J=8.1 Hz, 1 H) 7.82 (m, 1 H) 8.09 (ddd, J=8.1, 2.4, 1.1 Hz, 1 H) 8.26 (m, 1 H).
  • 48
  • [ 5892-99-9 ]
  • AZD2327 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: butyl magnesium bromide; n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -10 - -5 °C / Inert atmosphere 1.2: -40 - -20 °C 2.1: sulfurous dibromide / dichloromethane / 1 h / 20 °C 3.1: sulfurous dibromide / acetonitrile / 1 h / 65 °C 4.1: (2S,3S)-di-4-toluoyltartaric acid / ethanol / 12 h 5.1: sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 6.1: ammonium chloride; iron / ethanol; water; tetrahydrofuran / 24 h / 90 °C
Multi-step reaction with 5 steps 1.1: butyl magnesium bromide; n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -10 - -5 °C / Inert atmosphere 1.2: -40 - -20 °C 2.1: thionyl chloride / acetic acid butyl ester / 1.5 h / 35 - 45 °C 3.1: potassium carbonate; potassium iodide / butanone / 23 h / Reflux 4.1: hydrogen / platinum on carbon / isopropyl alcohol; water / 6 h / 40 °C 5.1: Chiralpak.(R). AD 20 micron / isopropyl alcohol; ethanol
  • 49
  • [ 5892-99-9 ]
  • [ 875647-78-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: butyl magnesium bromide; n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -10 - -5 °C / Inert atmosphere 1.2: -40 - -20 °C 2.1: thionyl chloride / acetic acid butyl ester / 1.5 h / 35 - 45 °C 3.1: potassium carbonate; potassium iodide / butanone / 23 h / Reflux 4.1: hydrogen / platinum on carbon / isopropyl alcohol; water / 6 h / 40 °C
  • 50
  • [ 5892-99-9 ]
  • [ 1309859-17-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: butyl magnesium bromide; n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -10 - -5 °C / Inert atmosphere 1.2: -40 - -20 °C 2.1: sulfurous dibromide / dichloromethane / 1 h / 20 °C 3.1: sulfurous dibromide / acetonitrile / 1 h / 65 °C 4.1: (2S,3S)-di-4-toluoyltartaric acid / ethanol / 12 h 5.1: sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 6.1: ammonium chloride; iron / ethanol; water; tetrahydrofuran / 24 h / 90 °C 7.1: hydrogenchloride / isopropyl alcohol; ethanol / 1 h / 55 °C
Multi-step reaction with 6 steps 1.1: butyl magnesium bromide; n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -10 - -5 °C / Inert atmosphere 1.2: -40 - -20 °C 2.1: thionyl chloride / acetic acid butyl ester / 1.5 h / 35 - 45 °C 3.1: potassium carbonate; potassium iodide / butanone / 23 h / Reflux 4.1: hydrogen / platinum on carbon / isopropyl alcohol; water / 6 h / 40 °C 5.1: Chiralpak.(R). AD 20 micron / isopropyl alcohol; ethanol 6.1: hydrogenchloride / isopropyl alcohol; ethanol / 1 h / 55 °C
  • 51
  • [ 5892-99-9 ]
  • 4-{(R)-(3-aminophenyl)[4-(4-fluorobenzyl)piperazin-1-yl]methyl}-N,N-diethylbenzamide trihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: butyl magnesium bromide; n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -10 - -5 °C / Inert atmosphere 1.2: -40 - -20 °C 2.1: sulfurous dibromide / dichloromethane / 1 h / 20 °C 3.1: sulfurous dibromide / acetonitrile / 1 h / 65 °C 4.1: (2S,3S)-di-4-toluoyltartaric acid / ethanol / 12 h 5.1: sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 6.1: ammonium chloride; iron / ethanol; water; tetrahydrofuran / 24 h / 90 °C 7.1: hydrogenchloride / isopropyl alcohol; tert-butyl methyl ether
Multi-step reaction with 6 steps 1.1: butyl magnesium bromide; n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -10 - -5 °C / Inert atmosphere 1.2: -40 - -20 °C 2.1: thionyl chloride / acetic acid butyl ester / 1.5 h / 35 - 45 °C 3.1: potassium carbonate; potassium iodide / butanone / 23 h / Reflux 4.1: hydrogen / platinum on carbon / isopropyl alcohol; water / 6 h / 40 °C 5.1: Chiralpak.(R). AD 20 micron / isopropyl alcohol; ethanol 6.1: hydrogenchloride / isopropyl alcohol; tert-butyl methyl ether
  • 52
  • [ 5892-99-9 ]
  • C29H35FN4O*(x)H2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: butyl magnesium bromide; n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -10 - -5 °C / Inert atmosphere 1.2: -40 - -20 °C 2.1: sulfurous dibromide / dichloromethane / 1 h / 20 °C 3.1: sulfurous dibromide / acetonitrile / 1 h / 65 °C 4.1: (2S,3S)-di-4-toluoyltartaric acid / ethanol / 12 h 5.1: sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 6.1: ammonium chloride; iron / ethanol; water; tetrahydrofuran / 24 h / 90 °C 7.1: sulfuric acid / ethyl acetate; isopropyl alcohol / 20 - 80 °C
Multi-step reaction with 6 steps 1.1: butyl magnesium bromide; n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -10 - -5 °C / Inert atmosphere 1.2: -40 - -20 °C 2.1: thionyl chloride / acetic acid butyl ester / 1.5 h / 35 - 45 °C 3.1: potassium carbonate; potassium iodide / butanone / 23 h / Reflux 4.1: hydrogen / platinum on carbon / isopropyl alcohol; water / 6 h / 40 °C 5.1: Chiralpak.(R). AD 20 micron / isopropyl alcohol; ethanol 6.1: sulfuric acid / ethyl acetate; isopropyl alcohol / 20 - 80 °C
  • 53
  • [ 5892-99-9 ]
  • 4-{(R)-(3-aminophenyl)[4-(4-fluorobenzyl)piperazin-1-yl]methyl}-N,N-diethylbenzamide phosphate acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: butyl magnesium bromide; n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -10 - -5 °C / Inert atmosphere 1.2: -40 - -20 °C 2.1: sulfurous dibromide / dichloromethane / 1 h / 20 °C 3.1: sulfurous dibromide / acetonitrile / 1 h / 65 °C 4.1: (2S,3S)-di-4-toluoyltartaric acid / ethanol / 12 h 5.1: sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 6.1: ammonium chloride; iron / ethanol; water; tetrahydrofuran / 24 h / 90 °C 7.1: phosphoric acid / ethanol; cyclopentylmethyl ether / 20 - 80 °C
Multi-step reaction with 6 steps 1.1: butyl magnesium bromide; n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -10 - -5 °C / Inert atmosphere 1.2: -40 - -20 °C 2.1: thionyl chloride / acetic acid butyl ester / 1.5 h / 35 - 45 °C 3.1: potassium carbonate; potassium iodide / butanone / 23 h / Reflux 4.1: hydrogen / platinum on carbon / isopropyl alcohol; water / 6 h / 40 °C 5.1: Chiralpak.(R). AD 20 micron / isopropyl alcohol; ethanol 6.1: phosphoric acid / ethanol; cyclopentylmethyl ether / 20 - 80 °C
  • 54
  • [ 55441-26-4 ]
  • [ 374564-35-9 ]
  • [ 5892-99-9 ]
  • 55
  • [ 64-10-8 ]
  • [ 5892-99-9 ]
  • [ 940532-00-3 ]
YieldReaction ConditionsOperation in experiment
291 mg With t-BuBrettPhos; palladium diacetate; caesium carbonate In tetrahydrofuran; water at 85℃; for 7h; Inert atmosphere;
  • 56
  • [ 5892-99-9 ]
  • [ 123-11-5 ]
  • [ 1321617-00-8 ]
YieldReaction ConditionsOperation in experiment
57% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver carbonate In tetrahydrofuran at 110℃; for 20h; Inert atmosphere; regioselective reaction;
  • 57
  • [ 617-84-5 ]
  • [ 873-75-6 ]
  • [ 5892-99-9 ]
YieldReaction ConditionsOperation in experiment
54% With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; In 1,1,2-trichloroethane; water; at 90℃; for 12h; General procedure: To a solution of alcohols 1 (0.1 mmol) in TCE (1.0 mL) was added n-Bu4NI (20 mol%) and N, N-disubstituted formamides 2 (0.5 mmol), followed by adding a solution of TBHP (6.0 equiv., 70% aqueous solution). The resulting mixture was stirred at 90 oC until it completed. When the reaction was finished, the reaction mixture was cooled to room temperature and poured into saturated Na2S2O3 solution (3.0 mL), extracted with EtOAc (3×8.0 mL), then washed with saturated brine. The combined organic layers were dried over anhydrous Na2SO4. After removing the solvents in vacuo, the residue was purified by flash column chromatography on silica gel or preparative TLC on GF 254 to afford the desired products 3.
65%Chromat. General procedure: Various N,N-dimethyl benzamides were obtained followinga simple procedure which involves charging the reactionmixture containing benzyl alcohols (1mmol), catalyst(20wt%) and DMF (5mL) into a two necked 50mL roundbottom flask (RBF) and stirred for 10min at RT and then70% aqueous TBHP (5mmol) was introduced dropwiseto the mixture under continuous stirring at RT. The RBFwas fitted with a water condenser and heated for 24h at100C. After 24h, the reaction mixture was cooled to RTand catalyst was then separated by filtration. The reactionmixture was diluted with 100mL of DW and extractedusing ethyl acetate (2 × 60mL). The combined organiclayer was dried using Na2SO4and concentrated underrotatory evaporator. The crude products were purified bychromatography using silica gel, hexane and ethyl acetate.Similarly a range of N,N-substituted benzamides werealso obtained by taking the stoichiometric amount of variousN-substituted formamides in 5mL of toluene keepingother parameters constant.
  • 58
  • [ 5892-99-9 ]
  • [ 185990-03-8 ]
  • N,N-diethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% Stage #1: dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane With potassium methanolate In 1,2-dimethoxyethane at 30℃; for 0.166667h; Inert atmosphere; Stage #2: N,N-diethyl-4-bromobenzamide In 1,2-dimethoxyethane at 30℃; for 1.25h;
51% Stage #1: dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane With potassium methanolate In 1,2-dimethoxyethane at 30℃; for 0.166667h; Inert atmosphere; Stage #2: N,N-diethyl-4-bromobenzamide In 1,2-dimethoxyethane at 30℃; for 1h;
  • 59
  • [ 5892-99-9 ]
  • [ 762-04-9 ]
  • [ 1450829-69-2 ]
YieldReaction ConditionsOperation in experiment
84% With dipotassium peroxodisulfate; silver sulfate In water; acetonitrile at 90℃; regioselective reaction;
  • 60
  • [ 617-84-5 ]
  • [ 16532-79-9 ]
  • [ 5892-99-9 ]
YieldReaction ConditionsOperation in experiment
With copper(I) oxide; 1,10-Phenanthroline; oxygen; toluene-4-sulfonic acid at 140℃; for 24h; Sealed tube;
  • 61
  • C8H15BrZn*LiCl [ No CAS ]
  • [ 5892-99-9 ]
  • (E)-N,N-diethyl-4-(3,4,4-trimethylpent-2-en-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With 2′-(dicyclohexylphophanyl)-N2,N2,N6,N6-tetramethyl[1,1′-biphenyl]-2,6-diamine; [(2-dicyclohexylphosphino-2’,6’-bis(N,N-dimethylamino)-1,1‘-biphenyl)-2-(2’-amino-1,1’-biphenyl)]palladium(II) methanesulfonate In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
  • 62
  • [ 586-76-5 ]
  • [ 5892-99-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride; N,N-dimethyl-formamide / toluene / 20 °C 2: triethylamine / dichloromethane / 0 - 20 °C
Multi-step reaction with 2 steps 1: thionyl chloride / Reflux; Inert atmosphere 2: triethylamine / Inert atmosphere
  • 63
  • [ 5892-99-9 ]
  • [ 79119-31-6 ]
YieldReaction ConditionsOperation in experiment
89% With cesiumhydroxide monohydrate; t-BuBrettPhos; C44H62NO5PPdS; water In 1,4-dioxane at 20℃; for 18h; Inert atmosphere;
  • 64
  • [ 100-42-5 ]
  • [ 5892-99-9 ]
  • [ 1620210-46-9 ]
YieldReaction ConditionsOperation in experiment
65% With bis(1,5-cyclooctadiene)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; 1,4-bis[bis(pentafluorophenyl)phosphino]butane In 1,4-dioxane at 100℃; for 48h; Sealed tube; Inert atmosphere;
  • 65
  • [ 1569-69-3 ]
  • [ 5892-99-9 ]
  • C17H25NOS [ No CAS ]
YieldReaction ConditionsOperation in experiment
98 %Spectr. With [(C6H3(OP(i-Pr)2)2)RhHCl]; sodium t-butanolate In toluene at 110℃; for 3h; Sealed tube; Inert atmosphere;
  • 66
  • [ 5892-99-9 ]
  • [ 22483-09-6 ]
  • C15H24N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; [(2-di-cyclohexylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1‘-biphenyl)-2-(2‘-amino-1,1’-biphenyl)]palladium(II) methanesulfonate; sodium t-butanolate In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; Schlenk technique;
  • 67
  • [ 618859-85-1 ]
  • [ 5892-99-9 ]
  • 5'-(tert-butyl)-N,N-diethyl-2'-(imidazo[1,5-a]pyridin-3-yl)[1,1'-biphenyl]-4-carboxamide [ No CAS ]
  • 5'-(tert-butyl)-N4,N4,N4'',N4''-tetraethyl-2'-(imidazo[1,5-a]pyridin-3-yl)-[1,1':3',1''-terphenyl]-4,4''-dicarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 69% 2: 9% With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; mesitylenecarboxylic acid; potassium carbonate In toluene at 130℃; for 15h; Inert atmosphere; Microwave irradiation; Glovebox; regioselective reaction;
  • 68
  • [ 201230-82-2 ]
  • [ 5467-74-3 ]
  • [ 109-89-7 ]
  • [ 5892-99-9 ]
YieldReaction ConditionsOperation in experiment
45% With N-chloro-succinimide; palladium 10% on activated carbon; sodium hydrogencarbonate In tert-butyl methyl ether at 45℃; for 18h; Inert atmosphere; Autoclave;
  • 69
  • C15H19IOZn [ No CAS ]
  • [ 5892-99-9 ]
  • (Z)-4-(2-cyclohexyl-1-(4-methoxyphenyl)vinyl)-N,N-diethylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel (0) In tetrahydrofuran; N,N-dimethyl acetamide at 70℃; for 16h; Inert atmosphere; Glovebox; Sealed tube;
  • 70
  • [ 201230-82-2 ]
  • [ 589-87-7 ]
  • [ 121-44-8 ]
  • [ 5892-99-9 ]
YieldReaction ConditionsOperation in experiment
89% With palladium 10% on activated carbon; oxygen In acetonitrile at 100℃; for 8h; Autoclave; Green chemistry;
  • 71
  • [ 201230-82-2 ]
  • [ 589-87-7 ]
  • [ 109-89-7 ]
  • [ 5892-99-9 ]
YieldReaction ConditionsOperation in experiment
91% With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 3h; Autoclave; chemoselective reaction; A typical procedure for aminocarbonylationreaction General procedure: Catalytic reactions were carried out in a Teflon-linedstainless steel autoclave (50 mL) equipped with a magneticstirrer bar and an automatic temperature controller. In atypical experiment, 0.5 mol% Pd, aryl iodide (1.0 mmol),amine (3.0 mmol) and K2CO3 (414.6 mg, 3.0 mmol) wereadded to DMF (4 mL) and allowed to react under COatmosphere (1 bar) at 120 C for 2-4 h. After the reaction,the reactor was cooled to room temperature. The reactionmixture was centrifuged at 5000 rpm for 10 min, and theclear supernatant, to which was added ethyl phenylacetateas an internal standard, was analyzed with GC. For the studyof substrate scope, after completion of the reaction, thecatalyst was centrifuged at 5000 rpm for 10 min and theclear supernatant was diluted with 20 % HCl and extractedwith diethyl ether. The organic layer was washed withsaturated NaHCO3 and NaCl solutions, respectively, driedover anhydrous Na2SO4 and evaporated under vacuum afterfiltration. The residue obtained was purified by columnchromatography (silica gel, 200-300 meshes; petroleum-ethyl acetate, 20:1) to afford the pure products. All productswere confirmed by 1H and 13C NMR analyses. For therecycling experiment, the solid catalyst was separated bycentrifugation from the reaction mixture, washed threetimes with the reaction solvent (DMF) and then engaged ina new catalytic cycle under the same reaction conditions.All the synthesized amides are known products, and wehave reported recently [28].
  • 72
  • [ 5892-99-9 ]
  • [ 73183-34-3 ]
  • N,N-diethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With C20H28Cl2CoFeNOP; potassium methanolate; methyllithium In tert-butyl methyl ether at 50℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;
69% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; Inert atmosphere; 39.6 Step 6: The mixture of 4-bromo-N,N-diethylbenzamide (2.8 g, 11.2 mmol), 4,4,4,4,5,5,5,5’- octamethyl-2,2’-bi(1,3,2-dioxaborolane) (3.4 g, 13.4 mmol), PdC12(dppf) (0.8 g, 1.12 mmol), and KOAc (2.2 g, 22.4 mmol) in dioxane (50 mL) protected under N2 atmosphere was heated to 90°C overnight. After cooling to room temperature, the mixture was concentrated. The residue was purified by the flash column chromatography (silica gel, eluting with DCM to 3% MeOH in DCM) to afford N,N-diethyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide as a brown solid (2.3 g, 69% yield). LC-MS (ESI): 303.9 (M + 1).
  • 73
  • [ 5892-99-9 ]
  • [ 1696-17-9 ]
YieldReaction ConditionsOperation in experiment
88% With triethylsilane; carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II) In toluene at 125 - 135℃; for 20h; Inert atmosphere; Sealed tube;
45% With 1,4-dioxane; 1,10-Phenanthroline; sodium hydride In mineral oil at 140℃; for 22h; Schlenk technique; Inert atmosphere;
37% With 2-(2-methoxyethoxy)ethyl alcohol; oxygen; sodium hydride In 1,4-dioxane at 20℃; for 24h; Schlenk technique; chemoselective reaction;
  • 74
  • [ 627-19-0 ]
  • [ 5892-99-9 ]
  • (E)-1-(4-(diethylcarbamoyl)phenyl)-3,3,4,4,5,5,5-heptafluoro-2-propylpent-1-en-1-yl trifluoromethane sulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; diisopropylamine; copper(l) iodide / 24 h / 80 °C / Inert atmosphere; Schlenk technique 2: copper(l) iodide / 1,2-dichloro-ethane / 15 h / Inert atmosphere; Schlenk technique; Heating; Sealed tube
  • 75
  • [ 627-19-0 ]
  • [ 5892-99-9 ]
  • N,N-diethyl-4-(pent-1-yn-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine at 80℃; for 24h; Inert atmosphere; Schlenk technique;
  • 76
  • [ 5892-99-9 ]
  • [ 667458-78-8 ]
  • 4-(N,N-diethylaminocarbonyl)phenylmethyl 3,5-bis(trifluoromethyl)phenylsulfone [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With palladium diacetate; caesium carbonate; tri tert-butylphosphoniumtetrafluoroborate at 120℃; for 24h; Sealed tube; Inert atmosphere; Schlenk technique;
  • 77
  • [ 5892-99-9 ]
  • [ 667458-78-8 ]
  • 2-((4’-(N,N-diethylaminocarbonyl)phenyl)(phenyl)methyl)benzo[d]oxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate; caesium carbonate / 24 h / 120 °C / Sealed tube; Inert atmosphere; Schlenk technique 2: lithium tert-butoxide; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,3-bis-(diphenylphosphino)propane / 1,4-dioxane / 12 h / 120 °C / Sealed tube; Inert atmosphere; Schlenk technique
  • 78
  • C15H39BO2Si4 [ No CAS ]
  • [ 5892-99-9 ]
  • C17H26BNO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: C15H39BO2Si4 With potassium <i>tert</i>-butylate In tetrahydrofuran at 30℃; for 0.166667h; Schlenk technique; Inert atmosphere; Stage #2: 4-bromo-N,N-diethylbenzamide With tetrabutyl ammonium fluoride In tetrahydrofuran at -10℃; for 2h; Schlenk technique; Inert atmosphere;
  • 79
  • [ 1391743-16-0 ]
  • [ 5892-99-9 ]
  • C25H25NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; bis[tris( 1,1-dimethylethyl)phosphine]-palladium In 1,2-dimethoxyethane; water at 80℃; for 12h;
  • 80
  • [ 4210-04-2 ]
  • [ 5892-99-9 ]
  • C20H19F6NO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With cyclopentyl methyl ether; palladium diacetate; lithium tert-butoxide; XPhos at 110℃; for 12h;
  • 81
  • [ 61117-58-6 ]
  • [ 99-99-0 ]
  • [ 5892-99-9 ]
  • C19H22N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With manganese; (1,2-dimethoxyethane)dichloronickel(II); 4,4'-Dimethoxy-2,2'-bipyridin; trimethylsilyl iodide In N,N-dimethyl-formamide at 120℃; for 16h;
  • 82
  • [ 201230-82-2 ]
  • [ 589-87-7 ]
  • [ 109-89-7 ]
  • [ 1267429-20-8 ]
  • [ 5892-99-9 ]
YieldReaction ConditionsOperation in experiment
30% With caesium carbonate In toluene at 80℃; for 20h; Microwave irradiation; Sealed tube;
  • 83
  • [ 5892-99-9 ]
  • [ 107-19-7 ]
  • N,N-diethyl-4-(3-hydroxyprop-1-ynyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
99.9% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 60℃; for 17h; 33.2 Step 2:Preparation of N,N-diethyl-4-(3-hydroxyprop-1-ynyl)benzamide The 4-bromo-N,N-diethylbenzamide (5.70 mg, 22.3 mmol) obtained in Step 1 and propargyl alcohol (2.60 ml, 44.5 mmol) were dissolved in triethylamine (100.00 ml), and stirred for 5 minutes. Bis(triphenylphosphine)palladium (II) dichloride (1.60 mg, 2.23 mmol) and copper iodide (I) (1.60 mg, 2.23 mmol) were added to the mixture, heated at 60 °C, refluxed, and stirred for 17 hours. The reaction solution was cooled at room temperature, concentrated under reduced pressure, and the obtained residue was diluted with ethyl acetate and washed with water and brine. An organic solvent layer was collected, dehydrated with anhydrous magnesium sulfate (MgSO4), filtered, and then concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (Hex:EA=1:1), thereby obtaining N,N-diethyl-4-(3-hydroxyprop-1-ynyl)benzamide (5.16 mg, 99.9% yield).
  • 84
  • [ 586-76-5 ]
  • [ 109-89-7 ]
  • [ 5892-99-9 ]
YieldReaction ConditionsOperation in experiment
92% With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 5h;
89% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diisopropylamine In water; N,N-dimethyl-formamide at 20℃; for 12h; 33.1 Step 1:Preparation of 4-bromo-N,N-diethylbenzamide 4-Bromobenzoic acid (5.00g, 24.9 mmol) was dissolved in N,N-dimethylformamide (100.00 ml), and mixed with diisopropylamine (13ml, 74.6 mmol). 1-Hydroxybenzotriazole hydrate (7.15 mg, 37.30 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.04 mg, 37.30 mmol) were added to the mixture, and stirred for 5 minutes. Diethylamine (3.1 ml, 37.3 mmol) was added to the mixture, and stirred at room temperature for 12 hours. The reaction solution was concentrated under reduced pressure, and the obtained residue was diluted with dichloromethane and washed with water and brine. An organic solvent layer was collected, dehydrated with anhydrous magnesium sulfate (MgSO4), filtered, and then concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (Hex:EA=3:1), thereby obtaining 4-bromo-N,N-diethylbenzamide (5.70 g, 89% yield).
73% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 20℃; 39.5 Step 5: The mixture of 4-bromobenzoic acid (3 g, 14.9 mmol), diethylamine (4.6 ml, 44.7 mmol), HATU (8.5 g, 22.3 mmol) and DIPEA (6.6 ml, 44.7 mmol) in DCM (30 mL) was stirred at room temperature overnight. Water (30 mL) was added, and then the mixture was extracted with EA three times. The combined organic layers were washed with water (20 mL x 3) and brine (20 mL x 1), dried over Na2SO4, filtered and concentrated. The residue was purified by the flash column chromatography (silica gel, eluting with PE to 20% EA in PE) to afford 4-bromo-N,N-diethylbenzamide as a brown oil (2.8 g, 73% yield). LC-MS (ESI): 256.9 (M + 1)
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;

  • 85
  • [ 873-73-4 ]
  • [ 5892-99-9 ]
  • C19H18ClNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With  di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; triethylamine In water at 45℃; for 22h; Inert atmosphere;
  • 86
  • [ 1211284-11-5 ]
  • [ 5892-99-9 ]
  • N,N-diethyl-4-[(3-phenyloxetan-3-yl)amino]benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; sodium t-butanolate; tert-butyl XPhos In water at 50℃; for 16h; Inert atmosphere;
  • 87
  • [ 591-87-7 ]
  • cesium 2-((1-methylcyclohexyl)oxy)-2-oxoacetate [ No CAS ]
  • [ 5892-99-9 ]
  • 2-(4-(diethylcarbamoyl)phenyl)-3-(1-methylcyclohexyl)propyl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With (1,2-dimethoxyethane)dichloronickel(II); [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; 4,4'-di-tert-butyl-2,2'-bipyridine In dimethyl sulfoxide at 35℃; for 24h; Sealed tube; Inert atmosphere; Irradiation; regioselective reaction;
  • 88
  • [ 5892-99-9 ]
  • C11H16BrN*ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: 4-bromo-N,N-diethylbenzamide With [κ2-{Ph2P(Se)NC9H6N}Al(Me)2]; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane at 20℃; for 12h; Schlenk technique; Glovebox; Stage #2: With hydrogenchloride In water chemoselective reaction;
  • 89
  • [ 5892-99-9 ]
  • (E)-4-(3-(dimethyl(phenyl)silyl)prop-1-en-1-yl)-N,N-diethylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrabutylammonium acetate; potassium carbonate; potassium chloride; palladium diacetate / N,N-dimethyl-formamide / 3 h / 90 °C / Inert atmosphere; Schlenk technique 1.2: 0.17 h / 20 °C / Inert atmosphere; Schlenk technique 2.1: methanol; sodium tetrahydroborate / 0 - 20 °C / Inert atmosphere; Schlenk technique 3.1: methylzinc chloride; dichlorobis(trimethylphosphine)nickel / tetrahydrofuran / 0.08 h / 20 °C / Inert atmosphere; Schlenk technique 3.2: 0.08 h / 20 °C / Inert atmosphere; Schlenk technique 3.3: 5 h / 80 °C / Inert atmosphere; Schlenk technique
  • 90
  • [ 5892-99-9 ]
  • (E)-N,N-diethyl-4-(3-hydroxyprop-1-en-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrabutylammonium acetate; potassium carbonate; potassium chloride; palladium diacetate / N,N-dimethyl-formamide / 3 h / 90 °C / Inert atmosphere; Schlenk technique 1.2: 0.17 h / 20 °C / Inert atmosphere; Schlenk technique 2.1: methanol; sodium tetrahydroborate / 0 - 20 °C / Inert atmosphere; Schlenk technique
  • 91
  • [ 3054-95-3 ]
  • [ 5892-99-9 ]
  • (E)-N,N-diethyl-4-(3-oxoprop-1-en-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: acrylaldehyde diethyl acetal; 4-bromo-N,N-diethylbenzamide With potassium chloride; tetrabutylammonium acetate; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 3h; Inert atmosphere; Schlenk technique; Stage #2: With hydrogenchloride In water at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique;
  • 92
  • [ 2996-92-1 ]
  • [ 5892-99-9 ]
  • N,N-diethyl-[1,1'-biphenyl]-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With potassium fluoride; propylene glycol; chloro-[2-(9-phenyl-1,10-phenanthrolin-2-yl)phenyl]palladium In dichloromethane at 100℃; for 12h; Inert atmosphere;
  • 93
  • [ 586-76-5 ]
  • [ 121-44-8 ]
  • [ 5892-99-9 ]
YieldReaction ConditionsOperation in experiment
78% With trifuran-2-yl-phosphane; palladium diacetate; 2,2-dimethylpropanoic anhydride In toluene at 150℃; for 15h; Inert atmosphere;
  • 94
  • benzyldimethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane [ No CAS ]
  • [ 5892-99-9 ]
  • 4-(benzyldimethylsilyl)-N,N-diethylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene at 80℃; for 72h; Inert atmosphere;
  • 95
  • [ 5892-99-9 ]
  • [ 99-92-3 ]
  • 4-((4-acetylphenyl)amino)-N,N-diethylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With sodium phenoxide; C47H70BrO4PPdSi In tetrahydrofuran at 75℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;
  • 96
  • [ 106-44-5 ]
  • [ 5892-99-9 ]
  • C18H21NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: 4-bromo-N,N-diethylbenzamide With potassium phosphate; N,N'-bis(2,5-dimethylpyrrol-1-yl)oxalamide; copper(I) bromide In dimethyl sulfoxide at 20℃; Inert atmosphere; Sealed tube; Glovebox; Stage #2: p-cresol In dimethyl sulfoxide at 100℃; Sealed tube; Inert atmosphere; Glovebox;
  • 97
  • [ 201230-82-2 ]
  • [ 5467-74-3 ]
  • [ 121-44-8 ]
  • [ 5892-99-9 ]
YieldReaction ConditionsOperation in experiment
75% With copper(l) iodide; oxygen; palladium dichloride In acetonitrile at 100℃; for 12h; Autoclave; High pressure;
  • 98
  • difluoroallyl boronate [ No CAS ]
  • [ 5892-99-9 ]
  • C14H17F2NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; N–phenyl–2–(dicyclohexylphosphino)pyrrole In 1,4-dioxane; 1,2-dimethoxyethane at 100℃; for 24h; Sealed tube; Inert atmosphere; regioselective reaction;
  • 99
  • 2-benzoyl-2-phenyl-2,3-dihydroquinazolin-4(1H)-one [ No CAS ]
  • [ 5892-99-9 ]
  • [ 67055-76-9 ]
YieldReaction ConditionsOperation in experiment
95% With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; Ni(cod)2*4,4'-di-tert-butyl-2,2'-bipyridine; sodium phosphate In N,N-dimethyl-formamide at 20℃; for 12h; Schlenk technique; Sealed tube; Irradiation; Inert atmosphere;
  • 100
  • [ 7677-24-9 ]
  • [ 5892-99-9 ]
  • 2-(4-bromophenyl)-2-(diethylamino)acetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% Stage #1: N,N-diethyl-4-bromobenzamide With Triethoxysilane; potassium-t-butoxide In toluene at 25℃; for 4h; Schlenk technique; Inert atmosphere; Stage #2: trimethylsilyl cyanide In toluene at 25℃; for 12h; Schlenk technique; Inert atmosphere;
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