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Product Details of [ 126909-78-2 ]

CAS No. :126909-78-2 MDL No. :MFCD12138830
Formula : C10H11BrO Boiling Point : -
Linear Structure Formula :- InChI Key :QYVPRMAOEXVFHH-UHFFFAOYSA-N
M.W : 227.10 Pubchem ID :15727633
Synonyms :

Safety of [ 126909-78-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 126909-78-2 ]

* 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 [ 126909-78-2 ]

[ 126909-78-2 ] Synthesis Path-Downstream   1~30

YieldReaction ConditionsOperation in experiment
96% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h; 280 Preparation Example 12: 2-chloro-6-cyclopentyloxypyridine General procedure: 6-chloro-2-pyridinol (1.95 g, 15 mmol) and K2CO3 (4.16 g, 30 mmol) were dissolved in 50 mL of DMF. Cyclopentylbromide (1.94 mL, 18 mmol) was added thereto, and the mixture was stirred at 80°C for 24 hours. Solids wereremoved, and the filtrate was concentrated to obtain the title compound (2.92 g, 98 %).
  • 3
  • [ 126909-78-2 ]
  • [ 96-22-0 ]
  • [ 1198223-21-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-bromo-3-(cyclopropylmethoxy)benzene With iodine; magnesium In tetrahydrofuran at 20℃; for 1.16667h; Stage #2: pentan-3-one In tetrahydrofuran at 20℃; for 2h; 12 Reference Example 12 Synthesis of 3-(3-(cyclopropylmethoxy)phenyl)pentan-3-amine [Show Image] To a solution of magnesium (280 mg) in THF (2.5 mL), iodine (10 mg) was added at room temperature. Then, a small amount of a solution of 1-bromo-3-(cyclopropylmethoxy)benzene (2.27 g) obtained according to a method described in the document (Izvestiya akademi Nauk SSSR, Seriya Khimicheskaya, 12, 2752-2755 (1989)) in THF (3.5 mL) was added thereto, and the mixture was stirred at room temperature for 10 minutes until the iodine color disappeared. The remaining amount of the solution of 1-bromo-3-(cyclopropylmethoxy)benzene in THF was added thereto, and the mixture was stirred at room temperature for 1 hour until the magnesium disappeared. To the reaction mixture, a solution of 3-pentanone (1.02 g) in THF (3.0 mL) was added, and the mixture was stirred at room temperature for 2 hours. To the reaction mixture, an aqueous saturated ammonium chloride solution (10 ml) was added at 0°C, and the aqueous layer was extracted with ethyl acetate (20 mL x 2). The organic layer was washed with brine (20 mL), dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30% ethyl acetate/hexane). The obtained compound was dissolved in chloroform (20 mL). To the solution, sodium azide (1.7 g) was added. To the reaction mixture, trifluoroacetic acid (3.2 mL) was added dropwise at 0°C, and the mixture was then stirred at room temperature for 1 hour. To the reaction mixture, water (20 mL) was added, and the resultant mixture was then extracted with chloroform (20 mL). The organic layer was washed with an aqueous saturated sodium bicarbonate solution (20 mL), dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10% ethyl acetate/hexane). The obtained compound was dissolved in methanol (10 mL). To the solution, 10% palladium-carbon (260 mg) was added, and the reaction mixture was stirred at room temperature for 2 hours under a hydrogen atmosphere. The precipitate was removed by filtration through a pad of Celite and washed with methanol (100 mL). Then, the combined filtrate was concentrated under reduced pressure to obtain the title compound (1.70 g) as a crude product.
  • 4
  • [ 126909-78-2 ]
  • [ 1198223-20-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: iodine; magnesium / tetrahydrofuran / 1.17 h / 20 °C 1.2: 2 h / 20 °C 2.1: sodium azide; trifluoroacetic acid / chloroform / 1 h / 0 - 20 °C 3.1: hydrogen / palladium 10% on activated carbon / methanol / 2 h / 20 °C
  • 5
  • [ 126909-78-2 ]
  • [ 1198223-22-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: iodine; magnesium / tetrahydrofuran / 1.17 h / 20 °C 1.2: 2 h / 20 °C 2.1: sodium azide; trifluoroacetic acid / chloroform / 1 h / 0 - 20 °C
  • 6
  • [ 591-20-8 ]
  • [ 7051-34-5 ]
  • [ 126909-78-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 4h; 79.6 Step-6: Synthesis of l-bromo-3-(cyclopropylmethoxy)benzene (12): To a stirred solution of 3-bromophenol 7 (20 g, 115.61 mmol) in dry DMF (80 mL), was added K2CO3 (31.7 g, 231.21 mmol) followed by (bromomethyl) cyclopropane (13.4 mL, 138.73 mmol) and the reaction mixture was stirred at 90 °C for 4h. The progress of the reaction was monitored by TLC. After completion of the reaction, reaction mixture was diluted with water and extracted with EtOAc. The combined organic layer was washed with water and brine, dried over anhydrous Na2S04 and concentrated under reduced pressure to afford 12 which was directly used for the next step. Yield: 22 g (crude). 1H NMR (400 MHz, chloroform-d3) δ 7.13 - 7.17 (m, 1 H), 7.03 - 7.09 (m, 2 H), 6.83-6.86 (m, 1 H), 3.79 (d, j=7.34 Hz, 2 H), 1.20 - 1.34 (m, 1 H), 0.62 - 0.71 (m, 2 H), 0.34-0.36 (m, 2 H).
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 4h; 43.1 Step-1: Synthesis of l-bromo-3-(cyclopropylmethoxy)benzene (23): To a stirred solution of 3-bromophenol 22 (20 g, 115.61 mmol) in dry DMF (80 mL), was added K2CO3 (31.7 g, 231.21 mmol) followed by (bromomethyl)cyclopropane (13.4 mL, 138.73 mmol) and the reaction mixture was stirred at 90 °C for 4h. The progress of the reaction was monitored by TLC. After completion of the reaction, reaction mixture was diluted with water and extracted with EtOAc. The combined organic layer was washed with water and brine, dried over anhydrous Na2S04 and concentrated under reduced pressure to afford 23 which was directly used for the next step. Yield: 22 g (crude). 1H NMR (400 MHz, CHLOROFORM-d3) δ 7.13 - 7.17 (m, 1 H), 7.03 - 7.09 (m, 2 H), 6.83-6.86 (m, 1 H), 3.79 (d, j=7.34 Hz, 2 H), 1.20 - 1.34 (m, 1 H), 0.62 - 0.71 (m, 2 H), 0.34-0.36 (m, 2 H).
With potassium carbonate In acetonitrile at 70℃; 170 Example 29j0061 9J Synthesis of 4-((5-ethoxybenzo jdj thiazol-2-yl)thio)- 1H- 1 ,2,3-triazole-5- carboxylic acid (29) General procedure: A mixture of 2-methylbenzo[d]thiazol-5-ol (Compound 29A) (2 g, 12.1 mmol), iodoethane (2.8 g, 18.2mmol), and potassium carbonate (3.4 g, 24.2mmol) in acetonitrile (40 mL) was stirred at 70 °C overnight. The mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate (50 mL), washed with H20 (10 mL x 3), dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 9% v/v) to give Compound 29B. LC-MS (ESI) m/z: 194 [M+H]t
With potassium carbonate In acetonitrile at 70℃; 170 Synthesis of 4-((5-ethoxybenzo[d]thiazol-2-yl)thio)-1H-1,2,3-triazole-5- carboxylic acid (29) A mixture of 2-methylbenzo[d]thiazol-5-ol (Compound 29A) (2 g, 12.1 mmol), iodoethane (2.8 g, 18.2mmol), and potassium carbonate (3.4 g, 24.2mmol) in acetonitrile (40 mL) was stirred at 70 °C overnight. The mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate (50 mL), washed with H2O (10 mL x 3), dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 9% v/v) to give Compound 29B. LC-MS (ESI) m/z: 194 [M+H]+.
With potassium carbonate In acetonitrile at 45℃; for 4h; 4.1.1.1 2-(4-((5′-Ethoxy-2′-methyl-[1,1′-biphenyl]-3-yl)methoxy)-2-fluorophenoxy)acetic acid (compound 1) General procedure: To a solution of 2a (600mg, 3.21mmol) and bromoethane (420mg, 3.85mmol) in acetonitrile was added K2CO3 (1330mg, 9.62mmol). The reaction mixture was heated to reflux with stirring for 4h. Then the reaction mixture was cooled to room temperature followed by filtration and the filtrate was concentrated under vacuum to obtain 600mg 3a (yield: 87%) as white solid.

  • 7
  • [ 126909-78-2 ]
  • N-(3-(cyclopropylmethoxy)phenyl)azetidine-3-amine trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis(dibenzylideneacetone)-palladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / toluene / 15 h / 110 °C 2: dichloromethane / 24 h / 19 - 24 °C
  • 8
  • [ 126909-78-2 ]
  • N-(1-(2-(3-((3-(cyclopropylmethoxy)phenyl)amino)azetidin-1-yl)-1,3-benzoxazol-6-yl)ethyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: bis(dibenzylideneacetone)-palladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / toluene / 15 h / 110 °C 2.1: dichloromethane / 24 h / 19 - 24 °C 3.1: Vilsmeier reagent / dichloromethane / 0.08 h / 0 °C 3.2: 1 h / 10 - 35 °C / Cooling with ice
  • 9
  • [ 193269-78-2 ]
  • [ 126909-78-2 ]
  • tert-butyl 3-((3-(cyclopropylmethoxy)phenyl)amino)azetidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
835 mg With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0) In toluene at 110℃; for 15h; 69.A A) tert-butyl 3-((3-(cyclopropylmethoxy)phenyl)amino)azetidine-1-carboxylate A) tert-butyl 3-((3-(cyclopropylmethoxy)phenyl)amino)azetidine-1-carboxylate (1053) A mixture of 559 tert-butyl 3-aminoazetidine-1-carboxylate (3.42 g), 560 1-bromo-3-(cyclopropylmethoxy)benzene (2.6 g), 561 (dibenzylidene)acetone-palladium(0) (3:2) (690 mg), 562 bis(2,2'-diphenylphosphonyl)-1,1'-binaphthyl (496 mg), 33 cesium carbonate (7.4 g) and 54 toluene (50 ml) was stirred at 110°C for 15 hr. The reaction mixture was filtered, 29 water was added and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate) and purified by HPLC (45 acetonitrile/water, 0.1% 236 ammonium carbonate added) to give the 563 title compound (835 mg). 1H NMR (400 MHz, DMSO-d6) δ 0.20-0.35 (2H, m), 0.46-0.60 (2H, m), 1.06-1.25 (1H, m), 1.38 (9H, s), 3.50-3.65 (2H, m), 3.71 (2H, d, J = 6.8 Hz), 4.02-4.21 (3H, m), 5.95-6.04 (1H, m), 6.07 (1H, dd, J = 8.0, 1.6 Hz), 6.15 (1H, dd, J = 8.0, 2.0 Hz), 6.21 (1H, d, J = 6.4 Hz), 6.96 (1H, t, J = 8.0 Hz).
  • 10
  • [ 126909-78-2 ]
  • 3-(cyclopropylmethoxy)-N-(pent-4-en-1-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tert.-butyl lithium / tetrahydrofuran / 0.5 h / -78 - 20 °C 1.2: 0.75 h / 0 °C 1.3: 1 h / 0 - 20 °C 2.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C
  • 11
  • [ 126909-78-2 ]
  • (E)-3-(cyclopropylmethoxy)-N-(6-(2,4-dioxoimidazolidin-1-yl)hex-4-en-1-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tert.-butyl lithium / tetrahydrofuran / 0.5 h / -78 - 20 °C 1.2: 0.75 h / 0 °C 1.3: 1 h / 0 - 20 °C 2.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C 3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / 20 °C
  • 12
  • [ 126909-78-2 ]
  • 3-(cyclopropylmethoxy)benzenesulfonyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-bromo-3-(cyclopropylmethoxy)benzene With tert.-butyl lithium In tetrahydrofuran at -78 - 20℃; for 0.5h; Stage #2: With sulfur dioxide In tetrahydrofuran at 0℃; for 0.75h; Stage #3: With N-chloro-succinimide In tetrahydrofuran; dichloromethane at 0 - 20℃; for 1h; 79.7 Step-7: Synthesis of 3-(cyclopropylmethoxy)benzenesulfonyl chloride (1): A stirred solution of 8 (13.5 g, 59.7 mmol) in dry THF (150 mL) at -78 °C was treated with t-BuLi(1.7 M in THF, 42.2 mL, 71.7 mmol) dropwise and then allowed to warm to room temperature and stirred for a further 30 min. The reaction mixture was purged with a stream of S02 gas over 45 min then cooled to 0 °C. A solution of NCS (7.9 g, 59.7 mmol) in DCM (150 mL) was added and the reaction mixture allowed to warm to room temperature and stirred for a further 1 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered and concentrated to afford 1 as thick oil. The compound was used as such for the next step without purification. Yield: 13.3 g (crude).
Stage #1: 1-bromo-3-(cyclopropylmethoxy)benzene With tert.-butyl lithium In tetrahydrofuran at -78 - 20℃; for 0.5h; Stage #2: With sulfur dioxide In tetrahydrofuran for 0.75h; Stage #3: With N-chloro-succinimide In tetrahydrofuran; dichloromethane at 0 - 20℃; for 1h; 43.2 Step-2: Synthesis of 3-(cyclopropylmethoxy)benzenesulfonyl chloride (15): A stirred solution of 23 (13.5 g, 59.7 mmol) in dry THF (150 mL) at -78 °C was treated with t-BuLi (1.7 M in THF, 42.2 mL, 71.7 mmol) dropwise and then allowed to warm to room temperature and stirred for a further 30 min. The reaction mixture was purged with a stream of S02 gas over 45 min then cooled to 0 °C. A solution of NCS (7.9 g, 59.7 mmol) in DCM (150 mL) was added and the reaction mixture allowed to warm to room temperature and stirred for a further 1 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered and concentrated to afford 15 as thick oil. The compound was used as such for the next step without purification. Yield: 13.3 g (crude).
  • 13
  • [ 126909-78-2 ]
  • 3-(cyclopropylmethoxy)-N-(6-(2,4-dioxoimidazolidin-1-yl)hexyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tert.-butyl lithium / tetrahydrofuran / 0.5 h / -78 - 20 °C 1.2: 0.75 h / 0 °C 1.3: 1 h / 0 - 20 °C 2.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C 3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / 20 °C 4.1: Rh/Al<SUB>2</SUB>O<SUB>3</SUB>; hydrogen / methanol / 1 h / 20 °C
  • 14
  • [ 126909-78-2 ]
  • 3-(cyclopropylmethoxy)-N-(3-(2-hydroxyethoxy)propyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tert.-butyl lithium / tetrahydrofuran / 0.5 h / -78 - 20 °C 1.2: 0.75 h 1.3: 1 h / 0 - 20 °C 2.1: triethylamine / dichloromethane / 0.17 h / 20 °C 2.2: 2 h / 0 - 20 °C
  • 15
  • [ 126909-78-2 ]
  • 2-(3-((3-(cyclopropylmethoxy)phenyl)sulfonamido)propoxy)ethyl methanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tert.-butyl lithium / tetrahydrofuran / 0.5 h / -78 - 20 °C 1.2: 0.75 h 1.3: 1 h / 0 - 20 °C 2.1: triethylamine / dichloromethane / 0.17 h / 20 °C 2.2: 2 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -20 - 20 °C
  • 16
  • [ 126909-78-2 ]
  • N-(3-(2-azidoethoxy)propyl)-3-(cyclopropylmethoxy)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tert.-butyl lithium / tetrahydrofuran / 0.5 h / -78 - 20 °C 1.2: 0.75 h 1.3: 1 h / 0 - 20 °C 2.1: triethylamine / dichloromethane / 0.17 h / 20 °C 2.2: 2 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C
  • 17
  • [ 126909-78-2 ]
  • N-(3-(2-aminoethoxy)propyl)-3-(cyclopropylmethoxy)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: tert.-butyl lithium / tetrahydrofuran / 0.5 h / -78 - 20 °C 1.2: 0.75 h 1.3: 1 h / 0 - 20 °C 2.1: triethylamine / dichloromethane / 0.17 h / 20 °C 2.2: 2 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C 5.1: hydrogen; palladium 10% on activated carbon / methanol / 1 h / 20 °C
  • 18
  • [ 126909-78-2 ]
  • N-(3-(2-cyanamidoethoxy)propyl)-3-(cyclopropylmethoxy)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: tert.-butyl lithium / tetrahydrofuran / 0.5 h / -78 - 20 °C 1.2: 0.75 h 1.3: 1 h / 0 - 20 °C 2.1: triethylamine / dichloromethane / 0.17 h / 20 °C 2.2: 2 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C 5.1: hydrogen; palladium 10% on activated carbon / methanol / 1 h / 20 °C 6.1: sodium hydrogencarbonate / tetrahydrofuran / 2 h / 0 - 20 °C
  • 19
  • [ 126909-78-2 ]
  • ethyl N-cyano-N-(2-(3-((3-(cyclopropylmethoxy)phenyl)sulfonamido)propoxy)ethyl)glycinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: tert.-butyl lithium / tetrahydrofuran / 0.5 h / -78 - 20 °C 1.2: 0.75 h 1.3: 1 h / 0 - 20 °C 2.1: triethylamine / dichloromethane / 0.17 h / 20 °C 2.2: 2 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C 5.1: hydrogen; palladium 10% on activated carbon / methanol / 1 h / 20 °C 6.1: sodium hydrogencarbonate / tetrahydrofuran / 2 h / 0 - 20 °C 7.1: potassium carbonate / acetonitrile / 16 h / 20 °C
  • 20
  • [ 126909-78-2 ]
  • 3-(cyclopropylmethoxy)-N-(3-(2-(2,4-dioxoimidazolidin-1-yl)ethoxy)propyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: tert.-butyl lithium / tetrahydrofuran / 0.5 h / -78 - 20 °C 1.2: 0.75 h 1.3: 1 h / 0 - 20 °C 2.1: triethylamine / dichloromethane / 0.17 h / 20 °C 2.2: 2 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C 5.1: hydrogen; palladium 10% on activated carbon / methanol / 1 h / 20 °C 6.1: sodium hydrogencarbonate / tetrahydrofuran / 2 h / 0 - 20 °C 7.1: potassium carbonate / acetonitrile / 16 h / 20 °C 8.1: dibutyl phosphate / toluene / 16 h / 100 °C
  • 21
  • [ 126909-78-2 ]
  • methyl 3-((2-(3-((3-(cyclopropylmethoxy)phenyl)sulfonamido)propoxy)ethyl)amino)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: tert.-butyl lithium / tetrahydrofuran / 0.5 h / -78 - 20 °C 1.2: 0.75 h 1.3: 1 h / 0 - 20 °C 2.1: triethylamine / dichloromethane / 0.17 h / 20 °C 2.2: 2 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C 5.1: hydrogen; palladium 10% on activated carbon / methanol / 1 h / 20 °C 6.1: chloroform / 16 h / 50 °C
  • 22
  • [ 126909-78-2 ]
  • methyl 3-(N-(2-(3-((3-(cyclopropylmethoxy)phenyl)sulfonamido)propoxy)ethyl)cyanamido)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: tert.-butyl lithium / tetrahydrofuran / 0.5 h / -78 - 20 °C 1.2: 0.75 h 1.3: 1 h / 0 - 20 °C 2.1: triethylamine / dichloromethane / 0.17 h / 20 °C 2.2: 2 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C 5.1: hydrogen; palladium 10% on activated carbon / methanol / 1 h / 20 °C 6.1: chloroform / 16 h / 50 °C 7.1: sodium hydrogencarbonate / tetrahydrofuran / 3 h / 0 - 20 °C
  • 23
  • [ 126909-78-2 ]
  • 3-(cyclopropylmethoxy)-N-(3-(2-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)ethoxy)propyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: tert.-butyl lithium / tetrahydrofuran / 0.5 h / -78 - 20 °C 1.2: 0.75 h 1.3: 1 h / 0 - 20 °C 2.1: triethylamine / dichloromethane / 0.17 h / 20 °C 2.2: 2 h / 0 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -20 - 20 °C 4.1: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C 5.1: hydrogen; palladium 10% on activated carbon / methanol / 1 h / 20 °C 6.1: chloroform / 16 h / 50 °C 7.1: sodium hydrogencarbonate / tetrahydrofuran / 3 h / 0 - 20 °C 8.1: dibutyl phosphate / toluene / 16 h / 100 °C
  • 24
  • [ 126909-78-2 ]
  • methyl 3-((3-(2-((3-(cyclopropylmethoxy)phenyl)sulfonamido)ethoxy)propyl)(ethoxycarbonyl)amino)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tert.-butyl lithium / tetrahydrofuran / 0.5 h / -78 - 20 °C 1.2: 0.75 h 1.3: 1 h / 0 - 20 °C 2.1: triethylamine / dichloromethane / 12 h / 0 - 20 °C
  • 25
  • [ 126909-78-2 ]
  • ethyl (3-amino-3-oxopropyl)(3-(2-((3-(cyclopropylmethoxy)phenyl)sulfonamido)ethoxy)propyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tert.-butyl lithium / tetrahydrofuran / 0.5 h / -78 - 20 °C 1.2: 0.75 h 1.3: 1 h / 0 - 20 °C 2.1: triethylamine / dichloromethane / 12 h / 0 - 20 °C 3.1: ammonium hydroxide / ethanol / 24 h / 20 °C / Sealed tube
  • 26
  • [ 126909-78-2 ]
  • 3-(cyclopropylmethoxy)-N-(2-(3-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)propoxy)ethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tert.-butyl lithium / tetrahydrofuran / 0.5 h / -78 - 20 °C 1.2: 0.75 h 1.3: 1 h / 0 - 20 °C 2.1: triethylamine / dichloromethane / 12 h / 0 - 20 °C 3.1: ammonium hydroxide / ethanol / 24 h / 20 °C / Sealed tube 4.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 4 h / 120 °C
  • 27
  • [ 126909-78-2 ]
  • C26H25FO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol; water / 24 h / 80 °C / Inert atmosphere 2.1: methanol; sodium tetrahydroborate / 0.5 h / 20 °C 2.2: 4 h 3.1: potassium carbonate; potassium iodide / acetonitrile / 12 h / 20 °C
  • 28
  • [ 126909-78-2 ]
  • 2-(4-((3′-(cyclopropylmethoxy)-[1,1′-biphenyl]-3-yl)methoxy)-2-fluorophenoxy)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol; water / 24 h / 80 °C / Inert atmosphere 2.1: methanol; sodium tetrahydroborate / 0.5 h / 20 °C 2.2: 4 h 3.1: potassium carbonate; potassium iodide / acetonitrile / 12 h / 20 °C 4.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 4 h / 20 °C
  • 29
  • [ 126909-78-2 ]
  • C17H17ClO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol; water / 24 h / 80 °C / Inert atmosphere 2.1: methanol; sodium tetrahydroborate / 0.5 h / 20 °C 2.2: 4 h
  • 30
  • [ 87199-16-4 ]
  • [ 126909-78-2 ]
  • C17H16O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 80℃; for 24h; Inert atmosphere; General procedure: The solution of 3a (600mg, 2.79mmol), (3-formylphenyl)boronic acid (460mg, 3.07mmol), Pd(PPh3)4 (390mg, 0.33mmol) and sodium carbonate (870mg, 8.37mmol) in toluene/ethanol/H2O (35mL, 3/1/3) was refluxed under nitrogen atmosphere for 24h. Then the mixture was diluted with saturated ammonium chloride solution and ethyl acetate, and the insoluble material was filtered through Celite. The organic layer of the filtrate was washed with water (25mL) and brine (25mL), dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography using a mixture of petroleum ether /ethyl acetate (10:1, v/v) as eluent to afford the desired product 4a 450mg (yield: 67%) as a white solid.
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