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Product Details of [ 1616828-53-5 ]

CAS No. :1616828-53-5 MDL No. :MFCD28658368
Formula : C9H7BrN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :IVHVBVMREUQUCX-UHFFFAOYSA-N
M.W : 255.06 Pubchem ID :136608334
Synonyms :

Safety of [ 1616828-53-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1616828-53-5 ]

* 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 [ 1616828-53-5 ]

[ 1616828-53-5 ] Synthesis Path-Downstream   1~101

  • 1
  • [ 1616828-53-5 ]
  • [ 1765-93-1 ]
  • [ 1616831-21-0 ]
YieldReaction ConditionsOperation in experiment
0.31 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 120℃; for 0.5h; Sealed tube; Microwave irradiation; 125.a a) 6- (4-Fluorophenyl)- 8-methoxyguinazolin-4(3H)-one a) 6- (4-Fluorophenyl)- 8-methoxyguinazolin-4(3H)-oneDichloro- 1,1 ‘-bis (diphenylphosphino)ferrocene palladium(II) (144 mg, 0.176 mmol) was added to a mixture of 6-bromo-8-methoxyquinazolin-4(3H)-one (example 2a, 700 mg, 2.74 mmol), 4- fluorophenylboronic acid (576 mg, 4.12 mmol) and cesium carbonate (1.79 g, 5.49 mmol) in dioxane (6 ml)/water (0.3 ml). The mixture was heated in a sealed tube under microwave irradiation at 120 °C for 30 minutes. Water (100 ml) was added. Extraction with dichloromethane/methanol (9:1) and chromatography (silica gel, methanol / dichloromethane = 0:100 to 10:90) yielded the title compound (0.31 g). MS: mle = 271.1 [M+Hf’.
  • 2
  • [ 1215634-37-9 ]
  • [ 60100-09-6 ]
  • [ 1616828-53-5 ]
YieldReaction ConditionsOperation in experiment
89% at 150℃; for 12h; 2.a a) 6-Bromo-8-methoxy-3H-guinazolin-4-one a) 6-Bromo-8-methoxy-3H-guinazolin-4-oneA suspension of 2-amino-5-bromo-3-methoxybenzoic acid hydrobromide (CAS Registry No.864293-44-7) (85.5 g, 261 mmol) in formamide (300 ml) was stuffed at 150 °C for 12 hours.After cooling to room temperature water (11) was added and the precipitate was filtered, triturated with water and dried. The title compound was isolated as an off-white solid (59.4 g, 89 %).MS: mle = 255.0 / 257.0 [M+H].
  • 3
  • [ 1616828-53-5 ]
  • [ 76513-69-4 ]
  • [ 1616829-35-6 ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: 6-bromo-8-methoxy-3H-quinazolin-4-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 60℃; for 1.5h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide; mineral oil at 20℃; for 72h; Cooling with ice; 49.a a) 6-Bromo-8-methoxy-3- ((2- (trimethylsilyl)ethoxy)methyl)guinazolin-4(3H)-one a) 6-Bromo-8-methoxy-3- ((2- (trimethylsilyl)ethoxy)methyl)guinazolin-4(3H)-one To a suspension of 6-bromo-8-methoxy-3H-quinazolin-4-one (lOg, 39 mmol) in dimethylformamide (150 ml) was added in 5 portions sodium hydride (2.6 g of a 55 % dispersionin mineral oil, 59 mmol). The mixture was stirred at 60 °C for 90 minutes. With ice bath cooling SEM-chloride (7.2 g, 43.1 mmol) was added dropwise. After 1 hours the temperature was allowed to reach 20 °C and stirring was continued for 3 d. All volatiles were evaporated and the residue was partitioned (ethyl acetate / brine). The organic layer was dried (Na2SO4), concentrated and chromatographed (silica gel, heptane / ethyl acetate = 100:0 to 0:100) and triturated with hexane to furnish the title compound as a white solid (7.2 g, 48 %). MS: mle =385.0 / 387.0 [M+Hf’.
  • 4
  • [ 128-09-6 ]
  • [ 1616828-53-5 ]
  • [ 1616830-92-2 ]
YieldReaction ConditionsOperation in experiment
67% With sulfuric acid at 20 - 60℃; for 104.5h; 117..a a) 6-Bromo-5-chloro-8 -methoxyguinazolin-4(3H)-one a) 6-Bromo-5-chloro-8 -methoxyguinazolin-4(3H)-one 6-Bromo-8-methoxyquinazolin-4(3H)-one (1.50 g, 5.88 mmol) was combined with sulfuric acid(66.2 g, 36 ml, 675 mmol) to give a brown suspension. At room temperature was added 1- chloropyrrolidine-2,5-dione (1.18 g, 8.82 mmol) in portions during a period of 10 minutes. After stifling for 15 minutes the two educts were completely dissolved. The mixture was stirred at room temperature for 23 hours. Part of the solution (12 ml) was removed for reaction control. Additional 1-chloropyffolidine-2,5-dione (0.79 g, 5.88 mmol) were added and the mixture washeated at 50 °C for 80 hours and then at 60 °C for 1.5 hours. After cooling to room temperature the mixture was added to ice/water and aqueous ammonium hydroxide (25 %, 100 ml) was added keeping the temperature below 10°C. The precipitate was filtered off and dried to yield the title compound as off-white solid (1.14 g, 67 %). MS: mle = 288.6 [M-H].
  • 5
  • [ 1616828-53-5 ]
  • [ 1616829-27-6 ]
YieldReaction ConditionsOperation in experiment
97% With sulfuric acid; nitric acid at 10℃; for 1h; Cooling with ice; 44.a a) 6-Bromo-8-methoxy-5-nitroguinazolin-4(3H)-one a) 6-Bromo-8-methoxy-5-nitroguinazolin-4(3H)-oneNitric acid (10 ml of a 65 % solution) was cooled in an ice bath and conc. sulfuric acid (10 ml) was added at a rate keeping temperature < 10°C. 6-Bromo-8-methoxy-3H-quinazolin-4-one (example 2a) was added in small portions keeping temperature < 10 °C. The mixture was stuffedin an ice bath for 1 hour, allowed to reach 20 °C and poured on ice (50 g). Filtration, washing with water and drying furnished the title compound as a grey solid (3.4 g, 97 %). MS: mle = 300.0 /298.1 [M-H].
  • 6
  • [ 1616828-53-5 ]
  • [ 1616828-60-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice
  • 7
  • [ 1616828-53-5 ]
  • [ 1616829-36-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1.5 h / 60 °C 1.2: 72 h / 20 °C / Cooling with ice 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / 1,4-dioxane / 3 h / 90 °C
  • 8
  • [ 1616828-53-5 ]
  • [ 1616829-37-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1.5 h / 60 °C 1.2: 72 h / 20 °C / Cooling with ice 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / 1,4-dioxane / 3 h / 90 °C 3.1: bromine; silver(II) sulfate / acetic acid / 16 h / 20 °C
  • 9
  • [ 1616828-53-5 ]
  • [ 1616828-61-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 1.5 h / 100 °C
  • 10
  • [ 1616828-53-5 ]
  • [ 1616829-44-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1.5 h / 60 °C 1.2: 72 h / 20 °C / Cooling with ice 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / 1,4-dioxane / 3 h / 90 °C 3.1: bromine; silver(II) sulfate / acetic acid / 16 h / 20 °C 4.1: <i>L</i>-proline / N,N-dimethyl-formamide / 22 h / 100 - 120 °C
  • 11
  • [ 1616828-53-5 ]
  • [ 1616829-43-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1.5 h / 60 °C 1.2: 72 h / 20 °C / Cooling with ice 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / 1,4-dioxane / 3 h / 90 °C 3.1: bromine; silver(II) sulfate / acetic acid / 16 h / 20 °C 4.1: <i>L</i>-proline / N,N-dimethyl-formamide / 22 h / 100 - 120 °C 5.1: boron tribromide / dichloromethane / 16 h / 20 °C
  • 12
  • [ 1616828-53-5 ]
  • [ 1616828-59-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 1.5 h / 100 °C 4: trifluoroacetic acid / dichloromethane / 4 h / 20 °C
  • 13
  • [ 1616828-53-5 ]
  • [ 1616828-63-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 1.5 h / 100 °C 4: palladium 10% on activated carbon; hydrogen / ethyl acetate / 16 h / 20 °C
  • 14
  • [ 1616828-53-5 ]
  • [ 1616828-64-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3.1: bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 0.5 h / 50 °C 3.2: 2 h
  • 15
  • [ 1616828-53-5 ]
  • [ 1616828-66-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene; tetrahydrofuran / 4 h / 20 °C 3.2: 2 h
  • 16
  • [ 1616828-53-5 ]
  • [ 1616829-69-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3.1: tributyl(3,6-dihydro-2H-pyran-4-yl)stannane; tetrakis(triphenylphosphine) palladium(0) / toluene / 2 h / Reflux 3.2: 3 h / Reflux 3.3: 1 h / 20 °C
  • 17
  • [ 1616828-53-5 ]
  • [ 1616829-70-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3.1: tributyl(3,6-dihydro-2H-pyran-4-yl)stannane; tetrakis(triphenylphosphine) palladium(0) / toluene / 2 h / Reflux 3.2: 3 h / Reflux 3.3: 1 h / 20 °C 4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 15 h / 25 °C
  • 18
  • [ 1616828-53-5 ]
  • [ 1616829-71-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3.1: tributyl(3,6-dihydro-2H-pyran-4-yl)stannane; tetrakis(triphenylphosphine) palladium(0) / toluene / 2 h / Reflux 3.2: 3 h / Reflux 3.3: 1 h / 20 °C 4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 15 h / 25 °C 5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / ethyl acetate / 4 h / 25 °C
  • 19
  • [ 1616828-53-5 ]
  • [ 1616829-68-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3.1: tributyl(3,6-dihydro-2H-pyran-4-yl)stannane; tetrakis(triphenylphosphine) palladium(0) / toluene / 2 h / Reflux 3.2: 3 h / Reflux 3.3: 1 h / 20 °C 4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 15 h / 25 °C 5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / ethyl acetate / 4 h / 25 °C 6.1: dichloromethane / 16 h / 25 °C
  • 20
  • [ 1616828-53-5 ]
  • [ 1616829-72-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3.1: tributyl(3,6-dihydro-2H-pyran-4-yl)stannane; tetrakis(triphenylphosphine) palladium(0) / toluene / 2 h / Reflux 3.2: 3 h / Reflux 3.3: 1 h / 20 °C 4.1: formic acid / water / 2 h / 90 °C / Sealed tube
  • 21
  • [ 1616828-53-5 ]
  • [ 1616829-74-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 4 h / 100 °C
  • 22
  • [ 1616828-53-5 ]
  • [ 1616829-73-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 4 h / 100 °C 4: formic acid / water / 2 h / 100 °C
  • 23
  • [ 1616828-53-5 ]
  • [ 1616829-76-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: 2,6-di-tert-butyl-4-methyl-phenol; tetrakis(triphenylphosphine) palladium(0) / toluene / Reflux
  • 24
  • [ 1616828-53-5 ]
  • [ 1616829-75-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: 2,6-di-tert-butyl-4-methyl-phenol; tetrakis(triphenylphosphine) palladium(0) / toluene / Reflux 4: formic acid / water / 1.5 h / 90 °C
  • 25
  • [ 1616828-53-5 ]
  • [ 1616829-78-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3.1: 2,6-di-tert-butyl-4-methyl-phenol; tetrakis(triphenylphosphine) palladium(0) / toluene / 20 h / Reflux 3.2: 0.5 h / 20 °C
Multi-step reaction with 3 steps 1.1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3.1: 1-methyl-2-tributylstannanyl-1H-imidazole; tetrakis(triphenylphosphine) palladium(0) / toluene / 20 h / Reflux 3.2: 0.5 h / 20 °C
  • 26
  • [ 1616828-53-5 ]
  • [ 1616829-77-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3.1: 2,6-di-tert-butyl-4-methyl-phenol; tetrakis(triphenylphosphine) palladium(0) / toluene / 20 h / Reflux 3.2: 0.5 h / 20 °C 4.1: formic acid / water / 1.5 h / 90 °C
Multi-step reaction with 4 steps 1.1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3.1: 1-methyl-2-tributylstannanyl-1H-imidazole; tetrakis(triphenylphosphine) palladium(0) / toluene / 20 h / Reflux 3.2: 0.5 h / 20 °C 4.1: formic acid / water / 1.5 h / 90 °C
  • 27
  • [ 1616828-53-5 ]
  • [ 1616829-83-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C / Sealed tube
  • 28
  • [ 1616828-53-5 ]
  • [ 1616829-82-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C / Sealed tube 5: formic acid / water / 80 - 100 °C
  • 29
  • [ 1616828-53-5 ]
  • [ 1616829-85-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C / Sealed tube
  • 30
  • [ 1616828-53-5 ]
  • [ 1616829-84-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C / Sealed tube 5: formic acid / water / 80 - 100 °C
  • 31
  • [ 1616828-53-5 ]
  • [ 1616829-87-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C / Sealed tube
  • 32
  • [ 1616828-53-5 ]
  • [ 1616829-86-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C / Sealed tube 5: formic acid / water / 80 - 100 °C
  • 33
  • [ 1616828-53-5 ]
  • [ 1616829-89-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C / Sealed tube
  • 34
  • [ 1616828-53-5 ]
  • [ 1616829-88-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C / Sealed tube 5: formic acid / water / 80 - 100 °C
  • 35
  • [ 1616828-53-5 ]
  • [ 1616829-95-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C / Sealed tube
  • 36
  • [ 1616828-53-5 ]
  • [ 1616829-94-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C / Sealed tube 5: formic acid / water / 80 - 100 °C
  • 37
  • [ 1616828-53-5 ]
  • [ 1616829-97-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C
  • 38
  • [ 1616828-53-5 ]
  • [ 1616829-96-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C 5: formic acid / water / 80 - 100 °C
  • 39
  • [ 1616828-53-5 ]
  • [ 1616829-99-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C
  • 40
  • [ 1616828-53-5 ]
  • [ 1616829-98-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C 5: formic acid / water / 80 - 100 °C
  • 41
  • [ 1616828-53-5 ]
  • [ 1616830-01-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide / 80 - 100 °C / Sealed tube
  • 42
  • [ 1616828-53-5 ]
  • [ 1616830-00-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide / 80 - 100 °C / Sealed tube 5: formic acid / water / 80 - 100 °C
  • 43
  • [ 1616828-53-5 ]
  • [ 1616830-03-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide / 80 - 100 °C / Sealed tube
  • 44
  • [ 1616828-53-5 ]
  • [ 1616830-02-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide / 80 - 100 °C / Sealed tube 5: formic acid / 80 - 100 °C
  • 45
  • [ 1616828-53-5 ]
  • [ 1616830-05-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide / 80 - 100 °C / Sealed tube
  • 46
  • [ 1616828-53-5 ]
  • [ 1616830-04-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide / 80 - 100 °C / Sealed tube 5: formic acid / water / 80 - 100 °C
  • 47
  • [ 1616828-53-5 ]
  • [ 1616830-07-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C
  • 48
  • [ 1616828-53-5 ]
  • [ 1616830-06-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C 5: formic acid / water / 80 - 100 °C
  • 49
  • [ 1616828-53-5 ]
  • [ 1616830-09-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C / Sealed tube
  • 50
  • [ 1616828-53-5 ]
  • [ 1616830-08-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C / Sealed tube 5: formic acid / water / 80 - 100 °C
  • 51
  • [ 1616828-53-5 ]
  • [ 1616830-11-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C
  • 52
  • [ 1616828-53-5 ]
  • [ 1616830-10-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C 5: formic acid / water / 80 - 100 °C
  • 53
  • [ 1616828-53-5 ]
  • [ 1616830-13-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C / Sealed tube
  • 54
  • [ 1616828-53-5 ]
  • [ 1616830-12-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C / Sealed tube 5: formic acid / water / 80 - 100 °C
  • 55
  • [ 1616828-53-5 ]
  • [ 1616830-15-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C
  • 56
  • [ 1616828-53-5 ]
  • [ 1616830-14-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C / Sealed tube 5: formic acid / water / 80 - 100 °C
  • 57
  • [ 1616828-53-5 ]
  • [ 1616830-17-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C
  • 58
  • [ 1616828-53-5 ]
  • [ 1616830-16-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C 5: formic acid / water / 80 - 100 °C
  • 59
  • [ 1616828-53-5 ]
  • [ 1616830-25-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 2 h / 100 °C
  • 60
  • [ 1616828-53-5 ]
  • [ 1616830-24-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 2 h / 100 °C 5: formic acid / water / 2 h / 100 °C
  • 61
  • [ 1616828-53-5 ]
  • [ 1616830-27-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 2 h / 100 °C
  • 62
  • [ 1616828-53-5 ]
  • [ 1616830-26-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 2 h / 100 °C 5: formic acid / water / 2 h / 90 °C
  • 63
  • [ 1616828-53-5 ]
  • [ 1616830-29-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C / Sealed tube 5: water; lithium hydroxide / tetrahydrofuran / 2 h / 60 °C
  • 64
  • [ 1616828-53-5 ]
  • [ 1616830-30-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C / Sealed tube 5: water; lithium hydroxide / tetrahydrofuran / 2 h / 60 °C 6: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C
  • 65
  • [ 1616828-53-5 ]
  • [ 1616830-28-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C / Sealed tube 5: water; lithium hydroxide / tetrahydrofuran / 2 h / 60 °C 6: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C 7: formic acid / N,N-dimethyl-formamide / 1.5 h / 100 °C
  • 66
  • [ 1616828-53-5 ]
  • [ 1616830-32-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 6 h / 90 °C
  • 67
  • [ 1616828-53-5 ]
  • [ 1616830-31-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 6 h / 90 °C 5: formic acid / water / 2 h / 100 °C
  • 68
  • [ 1616828-53-5 ]
  • [ 1616830-34-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 2 h / 100 °C
  • 69
  • [ 1616828-53-5 ]
  • [ 1616830-33-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 2 h / 100 °C 5: formic acid / water / 0.5 h / 100 °C
  • 70
  • [ 1616828-53-5 ]
  • [ 1616830-36-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 8.5 h / 100 °C
  • 71
  • [ 1616828-53-5 ]
  • [ 1616830-35-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 8.5 h / 100 °C 5: formic acid / water / 1.5 h / 100 °C
  • 72
  • [ 1616828-53-5 ]
  • [ 1616830-46-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C / Sealed tube 5: water; lithium hydroxide / tetrahydrofuran / 2 h / 60 °C 6: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C
  • 73
  • [ 1616828-53-5 ]
  • [ 1616830-45-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 80 - 100 °C / Sealed tube 5: water; lithium hydroxide / tetrahydrofuran / 2 h / 60 °C 6: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C 7: formic acid / water / 2 h / 90 °C
  • 74
  • [ 1616828-53-5 ]
  • [ 1616830-48-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 100 °C
  • 75
  • [ 1616828-53-5 ]
  • [ 1616830-47-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide; water / 100 °C 5: formic acid / water / 2 h / 100 °C
  • 76
  • [ 1616828-53-5 ]
  • [ 1616830-61-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 15 h / 100 °C
  • 77
  • [ 1616828-53-5 ]
  • [ 1616830-62-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 15 h / 100 °C 5: triethylamine / 3 h / 0 °C
  • 78
  • [ 1616828-53-5 ]
  • [ 1616830-63-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 15 h / 100 °C 5: triethylamine / 3 h / 0 °C 6: caesium carbonate / N,N-dimethyl-formamide / 20 °C
  • 79
  • [ 1616828-53-5 ]
  • 8-hydroxy-6-(4-((4-isopropylpiperazin-1-yl)methyl)-2-(methoxymethyl)phenyl)quinazolin-4(3H)-one tetrakis(2,2,2-trifluoroacetate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 15 h / 100 °C 5: triethylamine / 3 h / 0 °C 6: caesium carbonate / N,N-dimethyl-formamide / 20 °C 7: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
  • 80
  • [ 1616828-53-5 ]
  • [ 1616830-67-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 10 h / 100 °C
  • 81
  • [ 1616828-53-5 ]
  • 4-(8-hydroxy-4-oxo-3,4-dihydroquinazolin-6-yl)-3-(methoxymethyl)benzyl 4-isopropylpiperazine-1-carboxylate bis(2,2,2-trifluoroacetate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 15 h / 100 °C 5: triethylamine / 3 h / 0 °C 6: caesium carbonate / N,N-dimethyl-formamide / 20 °C 7: dichloromethane / 1 h / 20 °C
  • 82
  • [ 1616828-53-5 ]
  • [ 1616830-73-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane / 1.5 h / 130 °C
  • 83
  • [ 1616828-53-5 ]
  • 8-hydroxy-6-(2-(methoxymethyl)pyridin-3-yl)quinazolin-4(3H)-one bis (2,2,2-trifluoroacetate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane / 1.5 h / 130 °C 5: dichloromethane / 1 h / 20 °C
  • 84
  • [ 1616828-53-5 ]
  • [ 1616830-77-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane; water / 3 h / 90 °C
  • 85
  • [ 1616828-53-5 ]
  • [ 1616830-75-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane; water / 3 h / 90 °C 5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
  • 86
  • [ 1616828-53-5 ]
  • [ 1616830-79-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 3 h / 95 °C
  • 87
  • [ 1616828-53-5 ]
  • [ 1616830-78-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 3 h / 95 °C 4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
  • 88
  • [ 1616828-53-5 ]
  • [ 1616830-80-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 3 h / 95 °C 4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 5: tetrahydrofuran / 20 h / Reflux
  • 89
  • [ 1616828-53-5 ]
  • 6-(2-methylsulfanylmethyl-phenyl)-8-(2-trimethylsilanyl-ethoxymethoxy)-3-(2-trimethylsilanyl-ethoxymethyl)-3H-quinazolin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 15 h / 90 °C
  • 90
  • [ 1616828-53-5 ]
  • 8-hydroxy-6-(2-(methylsulfanylmethyl-phenyl)-3H-quinazolin-4-one) 2,2,2-trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 15 h / 90 °C 5: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
  • 91
  • [ 1616828-53-5 ]
  • [ 1616830-86-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 15 h / 90 °C 5: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.5 h / 0 - 25 °C
  • 92
  • [ 1616828-53-5 ]
  • [ 1616830-85-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 15 h / 90 °C 5: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.5 h / 0 - 25 °C 6: dichloromethane / 2 h / 20 °C
  • 93
  • [ 1616828-53-5 ]
  • [ 1616830-89-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 15 h / 90 °C
  • 94
  • [ 1616828-53-5 ]
  • [ 1616830-90-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogen bromide; water / acetic acid / 96 h / 130 °C 2: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 80 °C / Cooling with ice 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 15 h / 90 °C 5: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.5 h / 0 - 25 °C
  • 95
  • [ 1616828-53-5 ]
  • [ 1616828-54-6 ]
YieldReaction ConditionsOperation in experiment
93% With water; hydrogen bromide In acetic acid at 130℃; for 96h; 2.b b) 6-Bromo-8-hydroxy-3H-guinazolin-4-one b) 6-Bromo-8-hydroxy-3H-guinazolin-4-oneA solution of 6-bromo-8-methoxy-3H-quinazolin-4-one (45 g, 176 mmol) in a mixture of aqueous hydrobromic acid (135 ml of a 48 % solution), hydrobromic acid in acetic acid (190 ml of a 32 % solution) and acetic acid (190 ml) was stuffed at 130 °C for 4 days. The reactionmixture was allowed to reach room temperature and filtered. The precipitate was dried thoroughly and the title compound was isolated as an off-white solid (39.3 g, 93 %). MS: mle = 238.9 / 240.9 [M-H].
  • 96
  • [ 24424-99-5 ]
  • [ 1616828-53-5 ]
  • [ 1616831-30-1 ]
YieldReaction ConditionsOperation in experiment
0.45 g Stage #1: 6-bromo-8-methoxy-3H-quinazolin-4-one With boron tribromide In dichloromethane for 5h; Reflux; Stage #2: di-<i>tert</i>-butyl dicarbonate With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; 134.a a) 6-Bromo-4-oxo-3 ,4-dihydroguinazolin- 8-yl tert-butyl carbonate a) 6-Bromo-4-oxo-3 ,4-dihydroguinazolin- 8-yl tert-butyl carbonate1M Boron tribromide in dichloromethane (27.4 ml, 27.4 mmol) was added to a suspension of 6- bromo-8-methoxyquinazolin-4(3H)-one (1.0 g, 3.9 mmol) in dichloromethane (30 ml). The mixture was heated under reflux for 5 h. Methanol (10 ml) was added and the mixture was concentrated to a solid, addition of methanol and evaporation was repeated 2 times.Dichloromethane (100 ml) was added, followed by Hunig’s base (3.55 g, 4.79 ml, 27.4 mmol). Di-tert-butyl dicarbonate (1.28 g, 1.37 ml, 5.88 mmol) was added and the mixture was stuffed for 1 h at room temperature. The mixture was washed with saturated aqueous ammonium chloride and purified by chromatography (silica gel, ethyl acetate/heptane= 0:100 to 100:0) to give the title compound (0.45 g) as a white solid. MS: mle = 340.9 / 343.1 [M+H].
  • 97
  • [ 1616828-53-5 ]
  • [ 899436-71-6 ]
  • [ 1616831-37-8 ]
YieldReaction ConditionsOperation in experiment
0.1 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; at 130℃; for 0.5h;Microwave irradiation; a) 8-Methoxy-6- (2-methylpyridin-3-yl)guinazolin-4(3H)-oneA mixture of 6-bromo-8-methoxyquinazolin-4(3H)-one (0.15 g, 0.588 mmol), <strong>[899436-71-6]2-methylpyridin-3-ylboronic acid</strong> (0.12 g, 0.882 mmol), dichloro- 1,1 ?-bis (diphenylphosphino)ferrocenepalladium(II) (0.01 g, 0.12 mmol) and cesium carbonate (0.38 g, 1.18 mmol) in dioxane (2m1) / water (0.2 ml) was heated in a microwave oven for 30 mm at 130 C. The reaction mixture was poured on water and extracted with dichloromethane. The crude product was purified by chromatography (silica gel, ethyl acetate/methanol= 100:0 to 70:30) to give the title compound (0.10 g) as a light brown solid. MS: mle = 268.2 [M+Hf?.
  • 98
  • [ 891270-35-2 ]
  • [ 1616828-53-5 ]
  • [ 1616831-40-3 ]
YieldReaction ConditionsOperation in experiment
0.003 g Example 1418-Hydroxy-6-(4-pyrazol-1-yl-phenyl)-3H-quinazolin-4-oneA solution of cesium carbonate (0.10 g, 0.3 mmol) in water (0.25 ml) was added to a mixture ofbis(diphenylphosphino)feffocene palladium(II) (0.012 g, 15 jimol), 6-bromo-8-methoxyquinazolin-4(3H)-one (0.04 g, 0.15 mmol), and 4-( 1 H-pyrazol- 1 -yl)phenylboronic acid (0.04 g, 0.23 mmol) in dioxane (2.5 ml). The mixture was shaken in a sealed tube for 72 h at 100C and then concentrated. Acetic acid (0.4 ml), aqueous hydrobromic acid (48 %, 0.24 ml) and a solution of hydrobromic acid in acetic acid (33 %, 0.35 ml) were added to the residue. Themixture was shaken in a sealed tube at 150 C for 48 h. The mixture was concentrated and purified by chromatography (C18 reverse phase HPLC, acetonitrile / water (0.1 % formic acid) = 10:90 to 98:2) gave the title product (0.003 g). MS: mle = 305.1 [M+Hf?.
  • 99
  • [ 18997-19-8 ]
  • [ 1616828-53-5 ]
  • [ 1616831-46-9 ]
YieldReaction ConditionsOperation in experiment
0.32 g Stage #1: 6-bromo-8-methoxy-3H-quinazolin-4-one With boron tribromide In dichloromethane for 4h; Reflux; Stage #2: Chloromethyl pivalate With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 1h; 146.a a) (6-Bromo-4-oxo-3-(pivaloyloxymethyl)-3 ,4-dihydroguinazolin-8-yloxy)methyl pivalate a) (6-Bromo-4-oxo-3-(pivaloyloxymethyl)-3 ,4-dihydroguinazolin-8-yloxy)methyl pivalateBoron tribromide in dichloromethane (1M, 10.0 ml, 10.0 mmol) was added to6-bromo-8-methoxyquinazolin-4(3H)-one (0.26 g, 1.00 mmol) in dichloromethane (10 ml). Themixture was stuffed under reflux for 4 h. Methanol (10 ml) was added and the mixture concentrated to dryness. Addition of methanol and evaporation was repeated three times, and the residue was then dried under high vacuum. Potassium carbonate (0.69 g, 5.00 mmol) was added, followed by dimethylformamide (10.0 ml) and chloromethyl pivalate (0.45 g, 435 tl, 3.00 mmol). The mixture was stuffed at 100 °C for 1 h, and then filtered, and concentrated to an oil.The crude material was purified by flash chromatography (silica gel, 0 to 100 % ethyl acetate/heptane) to give the desired product (0.32 g) as a white solid. MS: mle = 496.2 [M+H].
  • 100
  • [ 864293-44-7 ]
  • [ 77287-34-4 ]
  • [ 1616828-53-5 ]
  • 101
  • [ 1616828-53-5 ]
  • 6-bromo-4-chloro-8-methoxyquinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% With trichlorophosphate at 120℃; for 1h; Microwave irradiation; C Step C: 6-bromo-4-chloro-8-methoxyquinazoline A sealable vial was charged with 6-bromo-8-methoxyquinazolin-4(3H)-one (0.49 g, 1.61 mmol) and phosphoryl chloride (5 mL). The resulting mixture was heated in a microwave reactor at 120 °C. After 1 h, the resulting mixture was cooled to rt and purified by FCC to afford 6-bromo-4- chloro-8-methoxyquinazoline (75 mg, 17%) as a white solid. MS (ESI): mass calcd. for C9H6BrClN2O, 271.94; m/z found, 273.0 [M+H]+.1H NMR (400 MHz, CDCl3) d 9.07 (s, 1H), 8.01 (d, J = 1.9 Hz, 1H), 7.37 (d, J = 1.8 Hz, 1H), 4.11 (s, 3H).
1.24 g With N,N-dimethyl-formamide In thionyl chloride for 5h; Reflux;
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