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[ CAS No. 113305-56-9 ]

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Product Details of [ 113305-56-9 ]

CAS No. :113305-56-9 MDL No. :MFCD01320680
Formula : C6H4INO3 Boiling Point : -
Linear Structure Formula :- InChI Key :QCKXOEOOXJUACP-UHFFFAOYSA-N
M.W :265.01 Pubchem ID :2733454
Synonyms :

Safety of [ 113305-56-9 ]

Signal Word:Danger Class:9
Precautionary Statements:P261-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P333+P313-P391-P501 UN#:3077
Hazard Statements:H302-H315-H317-H318-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 113305-56-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 113305-56-9 ]

[ 113305-56-9 ] Synthesis Path-Downstream   1~53

  • 1
  • [ 610-81-1 ]
  • [ 113305-56-9 ]
YieldReaction ConditionsOperation in experiment
89% A solution of NaNO2 (4.759 g, 68.982 mmol) in H2O (12 mL) was added dropwise to a mechanically stirred suspension of <strong>[610-81-1]4-amino-3-nitrophenol</strong> (5.316 g, 34.491 mmol) in concentrated HCl (12 mL) and H2O (2 mL) over 30 min at 0 ?. Subsequently, a solution of KI (11.451 g, 68.982 mmol) in H2O (10 mL) was added dropwise over 30 min at 0 ?. After the reaction mixture was stirred for 3 h at rt under dark, the precipitate was collected by filtration, washed with water and dried under vacuum. Silica gel column chromatography of crude product (n-hexane/Et2O = 4:1) afforded 6 (8.060 g, 30.414 mmol, 89 %) as orange crystalline solid.: Rf = 0.28 (n-hexane/Et2O = 2:1); IR (neat, cm-1) 3418, 1645, 1520, 1294, 1214; 1H NMR (400 MHz, CD3OD) delta 7.79 (d, 1H, J = 8.4 Hz), 7.26 (d, 1H, J = 2.8 Hz), 6.81 (dd, 1H, J = 8.4, 8.4 Hz), 4.69 (br s, OH); 13C NMR (100 MHz, CD3OD) delta 159.8, 155.5, 143.1, 122.2, 113.3, 72.5.
  • 2
  • [ 1878-94-0 ]
  • [ 113305-56-9 ]
  • 3
  • [ 113305-56-9 ]
  • [ 108-24-7 ]
  • 4-iodo-3-nitrophenyl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With dmap; triethylamine In dichloromethane at 20℃; for 9.5h; Inert atmosphere; Cooling with ice;
  • 4
  • [ 113305-56-9 ]
  • [ 100-39-0 ]
  • [ 183007-32-1 ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate In acetone 4-benzyloxy-1-iodo-2-nitrobenzene (7) To a solution of compound 6 (8.060 g, 30.414 mmol) and K2CO3 (8.407 g, 60.828 mmol) in acetone (20 ml) was added benzyl bromide (4.161 g, 24.331 mmol), and stirred at rt for overnight. The reaction mixture was filtered, washed with ether and the filtrate was purified by silica gel column chromatography (n-hexane/EtOAc = 8:1) affored 7 (10.298g, 28.999 mmol, 95 %) as yellow crystalline solid.: Rf = 0.56 (n-hexane/EtOAc = 4:1); IR (neat, cm-1) 3090, 3033, 2874, 1597, 1532, 1472, 1352, 1298, 1268, 1231, 1010; 1H NMR (400 MHz, CDCl3) δ 7.85 (d, 1H, J = 8.4 Hz), 7.48 (d, 1H, J = 3.0 Hz), 7.38 (m, 5H), 6.91 (dd, 1H, J = 8.4, 3.0 Hz), 5.09 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 159.1, 142.1, 135.2, 128.8, 128.5, 127.5, 121.1 112.0, 74.8, 70.7; MS (FAB) m/z 356.0 (M+H)+.
94% With potassium carbonate In acetone
  • 5
  • [ 1878-94-0 ]
  • [ 7697-37-2 ]
  • [ 113305-56-9 ]
  • 6
  • [ 1565-80-6 ]
  • [ 113305-56-9 ]
  • [ 604800-36-4 ]
YieldReaction ConditionsOperation in experiment
94% With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃;
94% With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
  • 7
  • [ 1111-97-3 ]
  • [ 113305-56-9 ]
  • [ 851857-15-3 ]
YieldReaction ConditionsOperation in experiment
91% With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone at 65℃; for 18h;
91% With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone at 23 - 65℃; for 18h; 2 3-Chloro-3-methyl-1-butyne (640 μL, 5.7 mmol, 3.0 equiv) was added to a stirred solution of 4-iodo-3-nitrophenol (500 mg, 1.89 mmol, 1 equiv), tetrabutylammonium iodide (2.10 g, 5.7 mmol, 3.0 equiv), and potassium carbonate (522 mg, 3.8 mmol, 2.0 equiv) in acetone (5.2 mL) at 23 °C. The reaction mixture was warmed to 65 °C and was heated at this temperature for 18 h. The product solution was allowed to cool to 23 °C, then was diluted with ethyl acetate (50 mL). The diluted product solution was washed with saturated aqueous sodium bicarbonate solution (5 mL) and saturated aqueous sodium chloride solution (5 mL). After washing, the organic layer was dried over sodium sulfate and the solids were filtered. The filtrate was concentrated. The residue obtained was dissolved in ethyl acetate (10 mL) and the resulting solution was filtered through a pad of Celite, eluting with ethyl acetate (50 mL). The eluent was concentrated and the residue obtained was purified by flash-column chromatography (4% acetone-hexanes) to furnish l-iodo-4-(2- methyl-3-butyn-2-yloxy)-2 -nitrobenzene as a pale yellow oil (569 mg, 91%).[00309] Rf= 0.55 (20% ethyl acetate-hexanes). 1H NMR (400 MHz, CDCl3), δ 7.88 (d, 1H, J = 8.8 Hz, H1), 7.78 (d, 1H, J = 2.8 Hz, H3), 7.14 (dd, 1H, J = 8.8, 2.8 Hz, H2), 2.67 (s, 1H, H4), 1.68 (s, 6H, CH3). 13C NMR (100 MHz, CDCl3), 8156.6, 153.3, 142.0, 126.1, 117.8, 84.6, 77.1, 75.9, 73.7, 29.6. IR (NaCl, thin film), cm-1 3290 (m), 2991 (w), 1532 (s). HRMS-EI (m/z): [M]+ calcd for C11H10INO3, 33θτ9706; found7330.9706:
  • 8
  • [ 112-35-6 ]
  • [ 113305-56-9 ]
  • [ 835629-17-9 ]
YieldReaction ConditionsOperation in experiment
95% With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃;
  • 9
  • [ 113305-56-9 ]
  • [ 88-11-9 ]
  • [ 914673-75-9 ]
YieldReaction ConditionsOperation in experiment
84% With potassium hydroxide In tetrahydrofuran; water at 20℃; for 16h;
  • 10
  • [ 910644-90-5 ]
  • [ 113305-56-9 ]
  • [ 910644-91-6 ]
YieldReaction ConditionsOperation in experiment
54% With triethylamine; copper(l) chloride In acetonitrile at 0 - 23℃;
54% With triethylamine; copper(l) chloride In acetonitrile
  • 11
  • [ 113305-56-9 ]
  • [ 835629-18-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2: 93 percent / FeCl3*6H20; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C
  • 12
  • [ 113305-56-9 ]
  • [ 835629-30-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl3*6H20; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO2 / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K2CO3 / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating
  • 13
  • [ 113305-56-9 ]
  • 3,3-diethyl-1-{2-iodo-5-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-phenyl}-1-triazene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl3*6H20; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO2 / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K2CO3 / acetonitrile / -5 - 20 °C
  • 14
  • [ 113305-56-9 ]
  • 3,3-diethyl-1-(2-ethynyl-5-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-phenyl)-1-triazene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl3*6H20; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO2 / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K2CO3 / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 5.1: K2CO3; methanol
  • 15
  • [ 113305-56-9 ]
  • 3,3-diethyl-1-[2-trimethylsilylethynyl-5-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-phenyl]-1-triazene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl3*6H20; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO2 / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K2CO3 / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating
  • 16
  • [ 113305-56-9 ]
  • C34H47N3O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl3*6H20; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO2 / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K2CO3 / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating 6.1: 87 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 7.1: 97 percent / K2CO3; methanol
Multi-step reaction with 7 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl3*6H20; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO2 / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K2CO3 / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 5.1: K2CO3; methanol 6.1: 87 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 7.1: 97 percent / K2CO3; methanol
  • 17
  • [ 113305-56-9 ]
  • C37H55N3O8Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl3*6H20; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO2 / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K2CO3 / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating 6.1: 87 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating
Multi-step reaction with 6 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl3*6H20; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO2 / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K2CO3 / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 5.1: K2CO3; methanol 6.1: 87 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating
  • 18
  • [ 113305-56-9 ]
  • C49H65N3O12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl3*6H20; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO2 / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K2CO3 / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating 6.1: 87 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 7.1: 97 percent / K2CO3; methanol 8.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 9.1: 97 percent / K2CO3; methanol / tetrahydrofuran
Multi-step reaction with 7 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl3*6H20; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO2 / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K2CO3 / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating 6.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 7.1: 97 percent / K2CO3; methanol / tetrahydrofuran
Multi-step reaction with 9 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl3*6H20; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO2 / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K2CO3 / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 5.1: K2CO3; methanol 6.1: 87 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 7.1: 97 percent / K2CO3; methanol 8.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 9.1: 97 percent / K2CO3; methanol / tetrahydrofuran
  • 19
  • [ 113305-56-9 ]
  • C52H73N3O12Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl3*6H20; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO2 / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K2CO3 / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating 6.1: 87 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 7.1: 97 percent / K2CO3; methanol 8.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating
Multi-step reaction with 6 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl3*6H20; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO2 / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K2CO3 / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating 6.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating
Multi-step reaction with 8 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl3*6H20; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO2 / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K2CO3 / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 5.1: K2CO3; methanol 6.1: 87 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 7.1: 97 percent / K2CO3; methanol 8.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating
  • 20
  • [ 113305-56-9 ]
  • C67H91N3O16Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl3*6H20; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO2 / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K2CO3 / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating 6.1: 87 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 7.1: 97 percent / K2CO3; methanol 8.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 9.1: 97 percent / K2CO3; methanol / tetrahydrofuran 10.1: 58 percent / Pd(PPh3)2Cl2; CuI; Et3N / tetrahydrofuran / Heating
Multi-step reaction with 8 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl3*6H20; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO2 / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K2CO3 / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating 6.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 7.1: 97 percent / K2CO3; methanol / tetrahydrofuran 8.1: 58 percent / Pd(PPh3)2Cl2; CuI; Et3N / tetrahydrofuran / Heating
Multi-step reaction with 6 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl3*6H20; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO2 / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K2CO3 / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating 6.1: 58 percent / Pd(PPh3)2Cl2; CuI; Et3N / tetrahydrofuran / Heating
Multi-step reaction with 10 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl3*6H20; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO2 / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K2CO3 / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 5.1: K2CO3; methanol 6.1: 87 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 7.1: 97 percent / K2CO3; methanol 8.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 9.1: 97 percent / K2CO3; methanol / tetrahydrofuran 10.1: 58 percent / Pd(PPh3)2Cl2; CuI; Et3N / tetrahydrofuran / Heating

  • 21
  • [ 113305-56-9 ]
  • C68H91N3O17Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl3*6H20; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO2 / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K2CO3 / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating 6.1: 87 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 7.1: 97 percent / K2CO3; methanol 8.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 9.1: 97 percent / K2CO3; methanol / tetrahydrofuran 10.1: 68 percent / Pd(PPh3)2Cl2; CuI; Et3N / tetrahydrofuran / Heating
Multi-step reaction with 8 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl3*6H20; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO2 / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K2CO3 / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 5.1: 90 percent / methyl iodide / 12 h / Heating 6.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 7.1: 97 percent / K2CO3; methanol / tetrahydrofuran 8.1: 68 percent / Pd(PPh3)2Cl2; CuI; Et3N / tetrahydrofuran / Heating
Multi-step reaction with 10 steps 1.1: 95 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2.1: 93 percent / FeCl3*6H20; Carbon bBlack; hydrazine / methanol / 2 h / 70 °C 3.1: aq. HCl; NaNO2 / acetonitrile / 0.5 h / -5 - 0 °C 3.2: 81 percent / aq. K2CO3 / acetonitrile / -5 - 20 °C 4.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 5.1: K2CO3; methanol 6.1: 87 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 7.1: 97 percent / K2CO3; methanol 8.1: 63 percent / Pd(PPh3)2Cl2; CuI; Et3N / Heating 9.1: 97 percent / K2CO3; methanol / tetrahydrofuran 10.1: 68 percent / Pd(PPh3)2Cl2; CuI; Et3N / tetrahydrofuran / Heating
  • 22
  • [ 113305-56-9 ]
  • [ 851857-06-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 91 percent / tetrabutylammonium iodide; K2CO3 / acetone / 18 h / 65 °C 2.1: 78 percent / 2,6-di-tert-butyl-4-methylphenol / m-xylene / 15 h / 140 °C 3.1: PhMgCl / tetrahydrofuran / 0.17 h / -40 °C 3.2: 44 percent / tetrahydrofuran / 0.5 h / -40 - 23 °C
  • 23
  • [ 113305-56-9 ]
  • [ 851959-12-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 91 percent / tetrabutylammonium iodide; K2CO3 / acetone / 18 h / 65 °C 2.1: 78 percent / 2,6-di-tert-butyl-4-methylphenol / m-xylene / 15 h / 140 °C 3.1: PhMgCl / tetrahydrofuran / 0.17 h / -40 °C 3.2: 44 percent / tetrahydrofuran / 0.5 h / -40 - 23 °C 4.1: 56 percent / aq. Ba(OH)2; 2-(di-tert-butylphosphino)biphenyl; tris(dibenzylideneacetone)dipalladium / tetrahydrofuran / 3 h / 23 - 40 °C 5.1: 49 percent / Zn; 1,2-dibromoethane; chlorotrimethylsilane / aq. NH4Cl / tetrahydrofuran; ethanol / 40 °C
Multi-step reaction with 4 steps 1: 91 percent / tetrabutylammonium iodide; K2CO3 / acetone / 18 h / 65 °C 2: 78 percent / 2,6-di-tert-butyl-4-methylphenol / m-xylene / 15 h / 140 °C 3: 72 percent / Cu; tris(dibenzylideneacetone)dipalladium / dimethylsulfoxide / 2 h / 70 °C 4: 49 percent / Zn; 1,2-dibromoethane; chlorotrimethylsilane / aq. NH4Cl / tetrahydrofuran; ethanol / 40 °C
  • 24
  • [ 113305-56-9 ]
  • C26H27N3O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 91 percent / tetrabutylammonium iodide; K2CO3 / acetone / 18 h / 65 °C 2.1: 78 percent / 2,6-di-tert-butyl-4-methylphenol / m-xylene / 15 h / 140 °C 3.1: PhMgCl / tetrahydrofuran / 0.17 h / -40 °C 3.2: 44 percent / tetrahydrofuran / 0.5 h / -40 - 23 °C 4.1: 56 percent / aq. Ba(OH)2; 2-(di-tert-butylphosphino)biphenyl; tris(dibenzylideneacetone)dipalladium / tetrahydrofuran / 3 h / 23 - 40 °C
Multi-step reaction with 3 steps 1: 91 percent / tetrabutylammonium iodide; K2CO3 / acetone / 18 h / 65 °C 2: 78 percent / 2,6-di-tert-butyl-4-methylphenol / m-xylene / 15 h / 140 °C 3: 72 percent / Cu; tris(dibenzylideneacetone)dipalladium / dimethylsulfoxide / 2 h / 70 °C
  • 25
  • [ 113305-56-9 ]
  • (-)-stephacidin B [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 91 percent / tetrabutylammonium iodide; K2CO3 / acetone / 18 h / 65 °C 2.1: 78 percent / 2,6-di-tert-butyl-4-methylphenol / m-xylene / 15 h / 140 °C 3.1: PhMgCl / tetrahydrofuran / 0.17 h / -40 °C 3.2: 44 percent / tetrahydrofuran / 0.5 h / -40 - 23 °C 4.1: 56 percent / aq. Ba(OH)2; 2-(di-tert-butylphosphino)biphenyl; tris(dibenzylideneacetone)dipalladium / tetrahydrofuran / 3 h / 23 - 40 °C 5.1: 49 percent / Zn; 1,2-dibromoethane; chlorotrimethylsilane / aq. NH4Cl / tetrahydrofuran; ethanol / 40 °C 6.1: 95 percent Spectr. / Et3N / acetonitrile / 3.5 h / 23 °C
Multi-step reaction with 5 steps 1: 91 percent / tetrabutylammonium iodide; K2CO3 / acetone / 18 h / 65 °C 2: 78 percent / 2,6-di-tert-butyl-4-methylphenol / m-xylene / 15 h / 140 °C 3: 72 percent / Cu; tris(dibenzylideneacetone)dipalladium / dimethylsulfoxide / 2 h / 70 °C 4: 49 percent / Zn; 1,2-dibromoethane; chlorotrimethylsilane / aq. NH4Cl / tetrahydrofuran; ethanol / 40 °C 5: 95 percent Spectr. / Et3N / acetonitrile / 3.5 h / 23 °C
  • 26
  • [ 113305-56-9 ]
  • [ 200814-22-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 91 percent / tetrabutylammonium iodide; K2CO3 / acetone / 18 h / 65 °C 2: 78 percent / 2,6-di-tert-butyl-4-methylphenol / m-xylene / 15 h / 140 °C
  • 27
  • [ 113305-56-9 ]
  • [ 604800-37-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C
  • 28
  • [ 113305-56-9 ]
  • [ 604800-40-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 72 percent / CH3I / 12 h / 110 °C
  • 29
  • [ 113305-56-9 ]
  • N,N-diethyl-N'-(2-iodo-5-((S)-2-methylbutoxy)phenyl)triazene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C
  • 30
  • [ 113305-56-9 ]
  • N,N-diethyl-N'-[2-ethynyl-5-((S)-2-methylbutoxy)phenyl]triazene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 80 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C
  • 31
  • [ 113305-56-9 ]
  • N,N-diethyl-N'-[2-trimethylsilylethynyl-5-((S)-2-methylbutoxy)phenyl]triazene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C
  • 32
  • [ 113305-56-9 ]
  • C30H39N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 72 percent / CH3I / 12 h / 110 °C 6.1: 65 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 7.1: 82 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C
Multi-step reaction with 7 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 80 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 6.1: 65 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 7.1: 82 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C
  • 33
  • [ 113305-56-9 ]
  • C33H47N3O2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 72 percent / CH3I / 12 h / 110 °C 6.1: 65 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C
Multi-step reaction with 6 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 80 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 6.1: 65 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C
  • 34
  • [ 113305-56-9 ]
  • [ 604800-47-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 72 percent / CH3I / 12 h / 110 °C 6.1: 65 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 7.1: 82 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C 9.1: 88 percent / CH3I / 6 h / 110 °C
Multi-step reaction with 7 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 72 percent / CH3I / 12 h / 110 °C 6.1: 60 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C 7.1: 88 percent / CH3I / 6 h / 110 °C
Multi-step reaction with 9 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 80 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 6.1: 65 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 7.1: 82 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C 9.1: 88 percent / CH3I / 6 h / 110 °C
  • 35
  • [ 113305-56-9 ]
  • C43H53N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 72 percent / CH3I / 12 h / 110 °C 6.1: 65 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 7.1: 82 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C 9.1: 100 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C
Multi-step reaction with 7 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 72 percent / CH3I / 12 h / 110 °C 6.1: 60 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C 7.1: 100 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C
Multi-step reaction with 9 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 80 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 6.1: 65 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 7.1: 82 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C 9.1: 100 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C
  • 36
  • [ 113305-56-9 ]
  • C46H61N3O3Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 72 percent / CH3I / 12 h / 110 °C 6.1: 65 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 7.1: 82 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C
Multi-step reaction with 6 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 72 percent / CH3I / 12 h / 110 °C 6.1: 60 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C
Multi-step reaction with 8 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 80 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 6.1: 65 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 7.1: 82 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C
  • 37
  • [ 113305-56-9 ]
  • C59H75N3O4Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 72 percent / CH3I / 12 h / 110 °C 6.1: 65 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 7.1: 82 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C 9.1: 100 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 10.1: 45 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C
Multi-step reaction with 8 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 72 percent / CH3I / 12 h / 110 °C 6.1: 60 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C 7.1: 100 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 8.1: 45 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C
Multi-step reaction with 6 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 72 percent / CH3I / 12 h / 110 °C 6.1: 45 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C
Multi-step reaction with 10 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 80 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 6.1: 65 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 7.1: 82 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C 9.1: 100 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 10.1: 45 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C

  • 38
  • [ 113305-56-9 ]
  • C85H103N3O6Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 72 percent / CH3I / 12 h / 110 °C 6.1: 65 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 7.1: 82 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C 9.1: 88 percent / CH3I / 6 h / 110 °C 10.1: 52 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C
Multi-step reaction with 10 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 72 percent / CH3I / 12 h / 110 °C 6.1: 65 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 7.1: 82 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C 9.1: 100 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 10.1: 52 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C
Multi-step reaction with 8 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 72 percent / CH3I / 12 h / 110 °C 6.1: 60 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C 7.1: 88 percent / CH3I / 6 h / 110 °C 8.1: 52 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C
Multi-step reaction with 8 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 72 percent / CH3I / 12 h / 110 °C 6.1: 60 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C 7.1: 100 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 8.1: 52 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C
Multi-step reaction with 10 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 80 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 6.1: 65 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 7.1: 82 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C 9.1: 88 percent / CH3I / 6 h / 110 °C 10.1: 52 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C
Multi-step reaction with 10 steps 1.1: 94 percent / PPh3; DIAD / tetrahydrofuran / 0 - 20 °C 2.1: FeCl3*6H2O; N2H4*H2O / carbon black / methanol / 2 h / 70 °C 3.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - 0 °C 3.2: 65 percent / K2CO3 / acetonitrile; H2O / 0.25 h / 20 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 5.1: 80 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 6.1: 65 percent / CuI; Et3N / PdCl2(PPh3)2 / 12 h / 45 °C 7.1: 82 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 8.1: 60 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C 9.1: 100 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C 10.1: 52 percent / CuI; Et3N / PdCl2(PPh3)2 / 45 °C

  • 39
  • [ 113305-56-9 ]
  • [ 443-31-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1: 94 percent / K2CO3 / acetone 2: 92 percent / Pd(OAc)2, (Tol)3P, Et3N / acetonitrile / Heating 3: 98 percent / Zn, AcOH 4: 96 percent / pyridine / CH2Cl2 5: 92 percent / triphosgene, Et3N / CH2Cl2 6: 1.) Bu3SnH, AIBN; 2.) dil. HCl / 1.) MeCN, reflux; 2.) 0 deg C 7: NaOH / H2O; tetrahydrofuran 8: H2 / Pd-C / methanol 9: DIBAL / CH2Cl2 / -78 °C 10: pyridine / CH2Cl2 / 0 °C 11: NaN3 / dimethylformamide 12: H2 / 10percent Pd-C / methanol
  • 40
  • [ 113305-56-9 ]
  • [ 682802-86-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 94 percent / K2CO3 / acetone 2: 92 percent / Pd(OAc)2, (Tol)3P, Et3N / acetonitrile / Heating 3: 98 percent / Zn, AcOH 4: 96 percent / pyridine / CH2Cl2 5: 92 percent / triphosgene, Et3N / CH2Cl2 6: 1.) Bu3SnH, AIBN; 2.) dil. HCl / 1.) MeCN, reflux; 2.) 0 deg C 7: NaOH / H2O; tetrahydrofuran 8: H2 / Pd-C / methanol 9: DIBAL / CH2Cl2 / -78 °C
  • 41
  • [ 113305-56-9 ]
  • [ 31031-05-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 94 percent / K2CO3 / acetone 2: 92 percent / Pd(OAc)2, (Tol)3P, Et3N / acetonitrile / Heating 3: 98 percent / Zn, AcOH 4: 96 percent / pyridine / CH2Cl2 5: 92 percent / triphosgene, Et3N / CH2Cl2 6: 1.) Bu3SnH, AIBN; 2.) dil. HCl / 1.) MeCN, reflux; 2.) 0 deg C 7: NaOH / H2O; tetrahydrofuran 8: H2 / Pd-C / methanol
  • 42
  • [ 113305-56-9 ]
  • 3-(2-Azido-ethyl)-1H-indol-6-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1: 94 percent / K2CO3 / acetone 2: 92 percent / Pd(OAc)2, (Tol)3P, Et3N / acetonitrile / Heating 3: 98 percent / Zn, AcOH 4: 96 percent / pyridine / CH2Cl2 5: 92 percent / triphosgene, Et3N / CH2Cl2 6: 1.) Bu3SnH, AIBN; 2.) dil. HCl / 1.) MeCN, reflux; 2.) 0 deg C 7: NaOH / H2O; tetrahydrofuran 8: H2 / Pd-C / methanol 9: DIBAL / CH2Cl2 / -78 °C 10: pyridine / CH2Cl2 / 0 °C 11: NaN3 / dimethylformamide
  • 44
  • [ 113305-56-9 ]
  • [ 6482-24-2 ]
  • [ 926297-19-0 ]
YieldReaction ConditionsOperation in experiment
86% With potassium carbonate; sodium iodide In acetone for 20h; Heating / reflux; 200 To a solution of 4-iodo-3-nitrophenol (5.33 g) in acetone (60 ml) were added 2-bromoethyl methyl ether (11.1 g) , sodium iodide (3.65 g) and potassium carbonate (6.98 g) , and the mixture was heated under reflux for 20 hr. The reaction mixture was concentrated, water was poured into the obtained residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The obtained residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-hexane (1:3, v/v) to give l-iodo-4- (2-methoxyethoxy) - 2-nitrobenzene (5.59 g, yield: 86%) as pale-yellow crystals. 1H-NMR (300 MHz, CDCl3) δ-'3.44 (3 H, s) , 3.76 (2 H, t, J = 4.5 Hz), 4.15 (2.H, t, J = 4.5 Hz), 6.90 (1 H, dd, J = 9.0, 2.7 Hz), 7.46 (1 H, d, J = 2.7 Hz), 7.87 (1 H, d, J = 9.0 Hz) .
  • 45
  • [ 113305-56-9 ]
  • [ 161270-70-8 ]
  • [ 960307-34-0 ]
YieldReaction ConditionsOperation in experiment
73% With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 23℃; for 16h;
73% With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 23℃; for 16h; [00221] Iodoarene 20. Diisopropyl azodicarboxylate (3.25 mL, 16.5 mmol, 1.1 equiv) was added dropwise to a solution of 4-iodo-3-nitrophenol (19) (3.98 g, 15.0 mmol, 1.0 equiv), the alcohol 18 (5.01 g, 16.5 mmol, 1.1 equiv), and triphenylphosphine (4.33 g, 16.5 mmol, 1.1 equiv) in tetrahydrofuran (37 mL). The orange solution was stirred at 23 0C for 16 hours. The product solution was concentrated in vacuo and the residue was recrystallized from chloroform, furnishing the iodoarene 20 (6.03 g, 73%) as a pale yellow solid. [00222] R/= 0.64 (hexanes-ethyl acetate 3 :2). 1H NMR (500 MHz, CDCl3), δ 7.86-7.83 (m, 3H), 7.71 (dd, 2H, J= 5.4, 2.9 Hz), 7.40 (d, IH, J= 2.4 Hz), 6.85 (dd, IH, J= 8.8, 2.9 Hz), 3.97 (t, 2H, J= 6.4 Hz), 3.68 (t, 2H, J= 7.3 Hz), 1.81-1.76 (m, 2H), 1.69-1.66 (m, 2H), 1.45-1.42 (m, 2H), 1.33-1.25 (m, 10H). 13C NMR (100 MHz, CDCl3), δ 168.7, 159.9, 153.7, 142.2, 134.1, 132.4, 123.4, 121.1, 111.7, 74.3, 69.1, 38.3, 29.6, 29.5, 29.4, 29.3, 29.1, 28.8, 27.0, 26.0. IR (NaCl, thin film), cm"1 2928(m), 2854(m), 1772(m), 1706(s). HRMS-ESI (m/z): [M + H]+ calcd for C24H28IN2O5+, 551.1037; found, 551.1039.
  • 46
  • [ 113305-56-9 ]
  • [ 824-94-2 ]
  • [ 1037305-13-7 ]
YieldReaction ConditionsOperation in experiment
89% With potassium carbonate In N,N-dimethyl-formamide
86% With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;
  • 48
  • [ 113305-56-9 ]
  • [ 98-80-6 ]
  • [ 51264-59-6 ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate In 1,4-dioxane at 90℃; for 2h; Inert atmosphere; Intermediate 165.2-nitrobiphenyl-4-oI To a solution of 4-iodo-3-nitrophenol (ig, 0.0037mo1) in dioxane (l0mL) was added potassium carbonate (2g, 0.014mo1) and phenyl boronic acid (0.6g, 0.0049mo1), the mixture was placed under nitrogen atmosphere and then norbornylphosphino Pd II (0.llg, 0.002mo1) was added into the reaction mixture, which was stirred for 2 hours at 90°C. The mixture was filtered through Celite and the solvent was removed under reduced pressure. The crude was partitioned between ethyl acetate and water, the organic layer was washed with brine, dried, filtered and the solvent was removed under reduced pressure giving the title compound as a solid (890mg, 95%), which was used in the next step without further purification.LRMS (mlz): 216 (M+1)+
  • 49
  • [ 3143-02-0 ]
  • [ 113305-56-9 ]
  • 3-[(4-Iodo-3-nitrophenoxy)methyl]-3-methyloxetane [ No CAS ]
YieldReaction ConditionsOperation in experiment
971 mg With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 18h; 17.1 Step 1: 3- [(4-Iodo-3 -nitrophenoxy)methyl] -3 -methyloxetane To a stirred mixture of 4-iodo-3-nitrophenol (1.02 g, 3.849 mmol), 3-methyl-3-oxetanemethanol (393 mg, 3.849 mmol) and triphenylphosphine (1.51 g, 5.773 mmol) in THF (20mL) was added a diethyl azadicaboxylate (DEAD) (0.91 mL, 5.773 mmol) at 0 °C. The reaction mixture was stirred at RT for 18 hours. The reaction mixture was concentrated under reduced pressure and the residue thus obtained was purified by silica gel column chromatography to yield 971 mg of the title product as yellow solid. ‘H NIVIR (300 MHz, CDC13) ö 1.44 (s, 3H), 4.07 (s, 2H), 4.48 (d, J 6.0 Hz, 2H), 4.60 (d, J= 6.0 Hz, 2H), 6.89-6.93 (m, 1H), 7.45-7.47 (m, 1H), 7.91 (d, J 8.7 Hz, 1H).
  • 50
  • [ 113305-56-9 ]
  • [ 98-09-9 ]
  • 4-iodo-3-nitrophenyl benzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With pyridine In dichloromethane for 16h; 2.a 4-Iodo-3-nitrophenylbenzenesulfonate (3E) a. 4-Iodo-3-nitrophenylbenzenesulfonate (3E) To a vial containing 4-iodo-3-nitrophenoli (1.03 g, 3.8 mmol, 1 equiv) in CH2Cl2 (8 mL) was added sequentially benzenesulphonyl chloride (0.73 mL, 5.7 mmol, 1.5 equiv), pyridine (0.9 mL, 11.4 mmol, 3 mmol), and the reaction was stirred for 16 hrs. After which the reaction was diluted with H2O (10 mL) and extracted with CH2Cl2 (2*10 mL). The combined organic layers were concentrated in vacuo and purified by column chromatography to afford the title compound as a yellow solid in 98% yield: Rf 0.47 (40:60, EtOAc/hex); 1H (CDCl3, 400 MHz) δ 8.00 (d, J=8.6 Hz, 1H), 7.88 (d, J=8.0 Hz, 2H), 7.80-7.70 (m, 1H), 7.64-7.56 (m, 2H), 7.47 (d, J=2.4 Hz, 1H); 13C (CDCl3, 100 MHz) δ 149.5, 142.9, 135.0, 134.4, 129.6, 128.5, 127.7, 119.9, 105.0, 84.1.
98% With pyridine In dichloromethane for 16h; 2.f f. *4-Iodo-3-nitrophenylbenzenesulfonate f. *4-Iodo-3-nitrophenylbenzenesulfonate (0158) To a vial containing 49 4-iodo-3-nitrophenol (1.03 g, 3.8 mmol, 1 equiv) in 11 CH2Cl2 (8 mL) was added sequentially 50 benzenesulphonyl chloride (0.73 mL, 5.7 mmol, 1.5 equiv), 51 pyridine (0.9 mL, 11.4 mmol, 3 mmol), and the reaction was stirred for 16 hrs. After which the reaction was diluted with H2O (10 mL) and extracted with CH2Cl2 (2×10 mL). The combined organic layers were concentrated in vacuo and purified by column chromatography to afford the 52 title compound as a yellow solid in 98% yield: Rf 0.47 (40:60, EtOAc/hex); 1H (CDCl3, 400 MHz) δ 8.00 (d, J=8.6 Hz, 1H), 7.88 (d, J=8.0 Hz, 2H), 7.80-7.70 (m, 1H), 7.64-7.56 (m, 2H), 7.47 (d, J=2.4 Hz, 1H); 13C (CDCl3, 100 MHz) δ 149.5, 142.9, 135.0, 134.4, 129.6, 128.5, 127.7, 119.9, 105.0, 84.1
  • 51
  • [ 113305-56-9 ]
  • [ 501-53-1 ]
  • [ 183007-32-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-iodo-3-nitrophenol With potassium carbonate In acetone for 0.0833333h; Stage #2: benzyl chloroformate In acetone for 4h; Reflux; 1 Step 1: Intermediate 38-b To a solution of 4-iodo-3-nitrophenol 38-a (3.0 g, 11.3 mmol) in acetone (113 ml) was added potassium carbonate (1.5 g, 11.3 mmol) and after stirring for 5 minutes, benzylbromide (1.3 ml, 11.3 mmol) was added. The reaction was stirred at reflux for 4 hours, then cooled to room temperature and filtered. Volatiles were removed under reduced pressure to provide Intermediate 38-b as a yellow solid.
  • 52
  • [ 113305-56-9 ]
  • [ 107-30-2 ]
  • 1-iodo-4-(methoxymethoxy)-2-nitrobenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
84g With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.5h; Cooling with ice; Inert atmosphere; 31 Reference Example 31:
1-iodo-4-(methoxymethoxy)-2-nitrobenzene Under a stream of nitrogen, to a solution of 4-iodo-3-nitrophenol (70.0 g) and N,N-diisopropylethylamine (68.2 g) in dichloromethane (370 mL), in the ice bath, chloromethyl methyl ether (31.8 g) was added dropwise. The resulting mixture was stirred at room temperature for 30 minutes. Water and ethyl acetate were added to the reaction mixture, followed by separation. The water layer was extracted with ethyl acetate, and the organic layer was washed with hydrochloric acid aqueous solution (0.5 mol/L), water, saturated sodium hydrogencarbonate aqueous solution, and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title compound (84.0 g) having the following physical property values. TLC: Rf 0.46 (hexane : ethyl acetate = 9:1); 1H-NMR (CDCl3): δ 3.47, 5.20, 6.98, 7.56, 7.87.
  • 53
  • [ 629-03-8 ]
  • [ 113305-56-9 ]
  • 4-[(6-bromohexyl)oxy]-1-iodo-2-nitrobenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% Stage #1: 4-iodo-3-nitrophenol With potassium carbonate In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; Stage #2: 1 ,6-dibromohexane In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;
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