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[ CAS No. 260809-26-5 ]

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Chemical Structure| 260809-26-5
Chemical Structure| 260809-26-5
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Product Details of [ 260809-26-5 ]

CAS No. :260809-26-5 MDL No. :MFCD09701229
Formula : C13H18BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :300.19 g/mol Pubchem ID :-
Synonyms :

Safety of [ 260809-26-5 ]

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 [ 260809-26-5 ]

  • Downstream synthetic route of [ 260809-26-5 ]

[ 260809-26-5 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 260809-26-5 ]
  • [ 7486-35-3 ]
  • tert-butyl methyl(4-vinylbenzyl)methylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: tert-butyl (4-bromobenzyl)(methyl)carbamate; tri-n-butyl(vinyl)tin With sodium fluoride In N,N-dimethyl-formamide at 80℃; Stage #2: With water; sodium fluoride In N,N-dimethyl-formamide at 20℃; for 4h; 24.1 (1) Production of tert-butyl methyl(4-vinylbenzyl)methylcarbamate: Tributyl(vinyl)stannane (2.34 mL, 7.99 mmol) and tetrakis(triphenylphosphine)palladium (385 mg, 0.33 mmol) were added to a DMF solution (20 mL) of tert-butyl (4-bromobenzyl)methylcarbamate (2.0 g, 6.66 mmol) (), and stirred overnight at 80°C in the presence of nitrogen. Saturated saline was added to the reaction liquid, then extracted with ether. Aqueous 5 wt.% sodium fluoride solution was added to the obtained organic layer, then stirred at room temperature for 4 hours. Next, water was added to the reaction liquid, and extracted with ethyl acetate. The obtained organic layer was washed with water and saturated saline, then dried with anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate = 10:0 to 17:3) to obtain the entitled compound (1.39 g, 84 %). 1H-NMR (400 MHz, CDCl3, δ ppm): 1.54 (9H, s), 2.70-2.90 (3H, m), 4.41 (2H, s), 5.23 (1H, d, J=10.6 Hz), 5.74 (1H, d, J=17.6 Hz), 6.70 (1H, dd, J=17.6, 10.6 Hz), 7.10-7.24 (2H, m), 7.37 (2H, d, J=8.0 Hz).
  • 2
  • [ 24424-99-5 ]
  • [ 26177-44-6 ]
  • [ 260809-26-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water 1.2: 18 h / 20 °C 2.1: silver(l) oxide / N,N-dimethyl-formamide / 18 h / 50 °C
  • 3
  • [ 68819-84-1 ]
  • [ 74-88-4 ]
  • [ 260809-26-5 ]
YieldReaction ConditionsOperation in experiment
With silver(l) oxide; In N,N-dimethyl-formamide; at 50℃; for 18h; In a 60-mL vial, tert-butyl-4-bromobenzylcarbamate (1.25 g, 4.37 mmol) was dissolved in DMF (12 mL). To this solution was added Ag2O (4.0 g, 17 mmol) followed by the addition of CH3I (0.68 mL, 11 mmol). The mixture was stirred at 50 C. for 18 hours. The reaction mixture was filtered through a bed of celite and the celite was washed with methanol (2*20 mL) and dichloromethane (2*20 mL). The filtrate was concentrated to remove most of the DMF. The residue was treated with water (50 mL) and a white emulsion formed. This mixture was extracted with ethyl acetate (4*25 mL), dried over Na2SO4, and the solvent was evaporated to yield tert-butyl-4-bromobenzyl(methyl)carbamate as a yellow oil. 1H NMR (300 MHz, DMSO-d6) delta 7.53 (d, J=8.1 Hz, 2H), 7.15 (d, J=8.4 Hz, 2H), 4.32 (s, 2H), 2.74 (s, 3H), 1.38 (s, 9H).
  • 4
  • [ 24424-99-5 ]
  • [ 699-03-6 ]
  • [ 260809-26-5 ]
  • 5
  • [ 260809-26-5 ]
  • 3-cyclopentyl-1-(tetrahydropyrimidin-1(2H)-yl)propan-1-one [ No CAS ]
  • tert-butyl-(4-(3-(3-cyclopentylpropanoyl)tetrahydropyrimidin-1(2H)-yl)benzyl)(methyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% With potassium <i>tert</i>-butylate; palladium diacetate; johnphos In toluene at 100℃; for 4h; Microwave irradiation; Inert atmosphere;
  • 6
  • [ 260809-26-5 ]
  • 3-cyclopentyl-1-(tetrahydropyrimidin-1(2H)-yl)propan-1-one [ No CAS ]
  • 3-cyclopentyl-1-(3-(4-((methylamino)methyl)phenyl)tetrahydropyrimidin-1(2H)-yl)propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: johnphos; potassium <i>tert</i>-butylate; palladium diacetate / toluene / 4 h / 100 °C / Microwave irradiation; Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 2 h / 22 °C
  • 7
  • [ 260809-26-5 ]
  • 3-(piperidin-4-yl)-1-(pyrrolidin-1-yl)propan-1-one [ No CAS ]
  • tert-butyl methyl(4-(4-(3-oxo-3-(pyrrolidin-1-yl)propyl)piperidin-1-yl)benzyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% With potassium <i>tert</i>-butylate; palladium diacetate; johnphos In toluene at 100℃; for 4h; Microwave irradiation; Inert atmosphere;
YieldReaction ConditionsOperation in experiment
45.3% With triethylamine In dichloromethane at 0 - 20℃; for 1h; Intermediate 2A: tert-buy1 ((6-chloropyridin--3--yl)methyl)carbamate General procedure: To a solution of (6chioropyridin3yl)methanamine (3.30 g, 23.1 mmol) inDCM (30 inL) was added TEA (4.84 mL. 34.7 rnmoi) and BOC2O (6.72 mL, 28.9 mrnol), at 0 °C. The resulting mixture was stirred at ambient temperature for iii. The reaction was quenched with saturated sodium bicarbonate solution (50 mL) and extracted with DCM (3x l0() rnL). The combined organic layers were washed with brine (100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain Intermediate 2A (5.50 g, 98.0%) as a yellow oil. ‘H NMR (300 MHz, DMSO-.ck) ö ppm1.38 (s, 9 H), 4,14 (d, J= 6.04 Hz, 2 H), 7.48 (d, J= 7.93 Hz, 2 H), 771 (dd, J= 8.12,2.46 Hz, I H), 8.28 (d, J = 189 Hz, I H). LCMS ,MethodD): retention time 2.31 mm,jM-H1-{i 243. 1.
  • 9
  • [ 260809-26-5 ]
  • (R)-tert-butyl 4-(6-((4-hydroxy-1-(4,4,4-trifluoro-3-phenylbutanoyl)piperidin-4- yl)methyl)-2-methyl-7-oxo-6,7-dihydro-2H-pyrazolo[4,3-d]pyrimidin-3-yl)benzyl(methyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 95 °C / Inert atmosphere 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate / 1,4-dioxane; water / 0.25 h / 150 °C / Inert atmosphere; Microwave irradiation
  • 10
  • [ 260809-26-5 ]
  • (R)-6-((4-hydroxy-1-(4,4,4-trifluoro-3-phenylbutanoyl)piperidin-4-yl)methyl)-2-methyl-3-(4-((methylamino)methyl)phenyl)-2H-pyrazolo[4,3-d]pyrimidin-7(6H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 95 °C / Inert atmosphere 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate / 1,4-dioxane; water / 0.25 h / 150 °C / Inert atmosphere; Microwave irradiation 3: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C
  • 11
  • [ 260809-26-5 ]
  • [ 73183-34-3 ]
  • [ 936728-17-5 ]
YieldReaction ConditionsOperation in experiment
94% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; for 14h; Inert atmosphere;
42% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 95℃; Inert atmosphere; 83.1 Step 1: tert-Butyl methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)carbamate: A solution of te/f-butyl 4-bromobenzyl(methyl)carbamate (150 mg, 0.50 mmol), (0909) bis(pinacolato)diboron (190 mg, 0.75 mmol) and potassium acetate (147 mg, 1.50 mmol) in anhydrous 1 ,4-dioxane (2 mL) was degassed by bubbling nitrogen through the solution for 10 min, followed by the addition of PdCI2(dppf)-DCM adduct (20 mg, 0.025 mmol). The reaction mixture was heated to 95 °C under a nitrogen atmosphere overnight, allowed to cool to RT, diluted with water (5 mL) and extracted into EtOAc (3 x 5 mL). The combined organic phases were dried over Na2S04, filtered, concentrated to dryness under reduced pressure, purified by flash chromatography (GraceResolv silica 12 g cartridge, (0910) cyclohexane:ethyl acetate, gradient elution from 95:5 to 70:30) to give the title compound (72 mg, 42%) as a colourless solid. LCMS (Method A): RT = 2.02 min, m/z = 292 [M- butene+H]+. NMR (300 MHz, CDCI3): δ 7.77 (d, 2H), 7.20 (br d, 2H), 4.43 (br s, 2H), 2.68- 2.89 (m, 3H), 1.39-1.53 (m, 9H), 1.33 (s, 12H).
  • 12
  • [ 260809-26-5 ]
  • C24H26BrN3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 14 h / 80 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; 1,4-dioxane / 16 h / 85 °C / Inert atmosphere
  • 13
  • [ 260809-26-5 ]
  • tert-butyl methyl(4-(1-oxo-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,4,6-tetrahydro-1H-azepino[5,4,3-cd]indol-5-yl)benzyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 14 h / 80 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; 1,4-dioxane / 16 h / 85 °C / Inert atmosphere 3: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 80 °C / Inert atmosphere
  • 14
  • [ 260809-26-5 ]
  • [18F]tert-butyl (4-(8-fluoro-1-oxo-2,3,4,6-tetrahydro-1H-azepino[5,4,3-cd]indol-5-yl)benzyl)(methyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 14 h / 80 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; 1,4-dioxane / 16 h / 85 °C / Inert atmosphere 3: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 80 °C / Inert atmosphere 4: 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosan/[18F]fluoride; tetrakis(pyridine)copper(II) bis(trifluoromethanesulfonate) / acetonitrile / 0.33 h / 120 °C / Sealed tube
  • 15
  • [ 260809-26-5 ]
  • [18F]rucaparib [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 14 h / 80 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; 1,4-dioxane / 16 h / 85 °C / Inert atmosphere 3: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 80 °C / Inert atmosphere 4: 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosan/[18F]fluoride; tetrakis(pyridine)copper(II) bis(trifluoromethanesulfonate) / acetonitrile / 0.33 h / 120 °C / Sealed tube 5: trifluoroacetic acid / acetonitrile / 0.33 h / 120 °C / Sealed tube
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