Alternatived Products of [ 35696-87-8 ]
Product Details of [ 35696-87-8 ]
CAS No. : | 35696-87-8 |
MDL No. : | MFCD09999820 |
Formula : |
C7H3Cl3O
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | LXQRQVUSDOKVLD-UHFFFAOYSA-N |
M.W : |
209.46
|
Pubchem ID : | 610194 |
Synonyms : |
|
Application In Synthesis of [ 35696-87-8 ]
* 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.
- Upstream synthesis route of [ 35696-87-8 ]
- Downstream synthetic route of [ 35696-87-8 ]
- 1
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[ 19735-89-8 ]
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[ 35696-87-8 ]
-
5-methyl-2-phenyl-4-((<i>Z</i>)-2,4,5-trichloro-benzylidene)-2,4-dihydro-pyrazol-3-one
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With ethanol |
|
- 2
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[ 19735-89-8 ]
-
[ 35696-87-8 ]
-
5,5'-dimethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-(2,4,5-trichloro-benzylidene)-bis-pyrazol-3-one
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
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With piperidine; ethanol |
|
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With sodium hydroxide; ethanol |
|
- 3
-
[ 60-80-0 ]
-
[ 35696-87-8 ]
-
1,5,1',5'-tetramethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-(2,4,5-trichloro-benzylidene)-bis-pyrazol-3-one
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With acetic anhydride |
|
- 4
-
[ 35696-87-8 ]
-
[ 83-40-9 ]
-
3-(3'-carboxy-2,4,5-trichloro-4'-hydroxy-5'-methyl-benzhydrylidene)-5-methyl-6-oxo-cyclohexa-1,4-dienecarboxylic acid
[ No CAS ]
- 5
-
[ 35696-87-8 ]
-
[ 127-09-3 ]
-
[ 32609-05-5 ]
Yield | Reaction Conditions | Operation in experiment |
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With acetic anhydride |
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- 6
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[ 35696-87-8 ]
-
[ 14299-54-8 ]
Yield | Reaction Conditions | Operation in experiment |
|
With diethyl ether; methylmagnesium bromide |
|
- 7
-
[ 35696-87-8 ]
-
4-chloro-6-formyl-benzene-1,3-disulfonic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With sodium sulfite unter Druck; |
|
- 8
-
[ 35696-87-8 ]
-
[ 372-09-8 ]
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2-cyano-3<i>t</i>-(2,4,5-trichloro-phenyl)-acrylic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With sodium hydroxide |
|
- 9
-
[ 79-24-3 ]
-
[ 35696-87-8 ]
-
[ 53581-89-8 ]
Yield | Reaction Conditions | Operation in experiment |
|
With ammonium acetate In acetic acid |
|
- 10
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[ 53581-87-6 ]
-
[ 35696-87-8 ]
Yield | Reaction Conditions | Operation in experiment |
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(i) SnCl2*2H2O, aq. HCl, (ii) aq. NaNO2, (iii) CuCl, aq. HCl; Multistep reaction; |
|
- 11
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[ 3955-26-8 ]
-
[ 35696-87-8 ]
Yield | Reaction Conditions | Operation in experiment |
|
With sulfuric acid |
|
- 12
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[ 75-17-2 ]
-
[ 636-30-6 ]
-
[ 35696-87-8 ]
Yield | Reaction Conditions | Operation in experiment |
|
(i) aq. HCl, NaNO2, (ii) /BRN= 1697325/, aq. NH3, (iii) aq. CuSO4, Na2SO3, NaOAc, (iv) aq. HCl; Multistep reaction; |
|
Yield | Reaction Conditions | Operation in experiment |
|
With sulfuric acid |
|
|
With water at 260℃; |
|
|
With sulfuric acid |
|
|
With sulfuric acid at 90 - 100℃; |
|
- 14
-
[ 35696-87-8 ]
-
[ 50-82-8 ]
Yield | Reaction Conditions | Operation in experiment |
96% |
In methanol; acetone; |
B. Synthesis of 2,4,5-Trichlorobenzoic Acid 9 2,4,5-Trichlorobenzaldehyde (0.275 g., 1.31 mmol) is dissolved in 8 mL acetone. A slight excess of Jones Reagent is added, and the mixture stirred at room temperature for 1 hour. Methanol (~6 mL) is added, and after 5 minutes the mixture is partitioned between methylene chloride and water. The aqueous phase is extracted with chloroform (2*), and the combined organic extracts are washed with water, then brine. The organic phase is dried (MgSO4), and concentrated to afford pure 2,4,5-trichlorobenzoic acid 9 (0.285 g., 1.26 mmol; 96% yield) as a white solid. 1H-NMR (300 MHz, CDCl3): delta 8.01 (s, 1H, ArH), 7.61 (s, 1H, ArH). |
- 15
-
[ 208512-51-0 ]
-
[ 35696-87-8 ]
Yield | Reaction Conditions | Operation in experiment |
79% |
Stage #1: 3-(2,4,5-trichloro-phenyl)-acrylic acid <i>tert</i>-butyl ester With ozone In dichloromethane at -78℃;
Stage #2: With dimethylsulfide In dichloromethane at -78 - 20℃; |
|
- 16
-
[ 68-12-2 ]
-
[ 120-82-1 ]
-
[ 35696-87-8 ]
-
[ 56961-75-2 ]
- 17
-
[ 35696-87-8 ]
-
C7H4Cl3NO
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With hydroxylamine hydrochloride; sodium carbonate In methanol; water at 20℃; for 3h; |
|
Reference:
[1]Wang, Xi-Zhao; Jia, Jiong; Zhang, Yan; Xu, Wei-Ren; Liu, Wei; Shi, Fang-Niu; Wang, Jian-Wu
[Journal of the Chinese Chemical Society, 2007, vol. 54, # 3, p. 643 - 652]
- 18
-
[ 35696-87-8 ]
-
[ 208512-53-2 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 96 percent / Jones reagent / acetone / 1 h / 20 °C
2: 70 percent / H2SO4 conc. / dioxane / 19 h / -78 °C |
|
- 19
-
[ 35696-87-8 ]
-
[ 208512-56-5 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: 96 percent / Jones reagent / acetone / 1 h / 20 °C
2: 70 percent / H2SO4 conc. / dioxane / 19 h / -78 °C
3: 81 percent / dimethylformamide / 0.83 h / 20 °C
4: 92 percent / CF3CO2H / CH2Cl2 / 4 h / 20 °C |
|
- 20
-
[ 35696-87-8 ]
-
[ 208512-54-3 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: 96 percent / Jones reagent / acetone / 1 h / 20 °C
2: 70 percent / H2SO4 conc. / dioxane / 19 h / -78 °C
3: 81 percent / dimethylformamide / 0.83 h / 20 °C |
|
- 21
-
[ 35696-87-8 ]
-
[ 415926-78-2 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: 96 percent / Jones reagent / acetone / 1 h / 20 °C
2: 70 percent / H2SO4 conc. / dioxane / 19 h / -78 °C
3: 81 percent / dimethylformamide / 0.83 h / 20 °C
4: 72 percent / aq. NaOH / tetrahydrofuran / 1.5 h / 20 °C |
|
- 22
-
[ 35696-87-8 ]
-
[ 208512-58-7 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: 96 percent / Jones reagent / acetone / 1 h / 20 °C
2: 70 percent / H2SO4 conc. / dioxane / 19 h / -78 °C
3: 81 percent / dimethylformamide / 0.83 h / 20 °C
4: 92 percent / CF3CO2H / CH2Cl2 / 4 h / 20 °C
5: 49 percent / dicyclohexylcarbodiimide / CH2Cl2 / 2 h / 20 °C |
|
- 23
-
[ 35696-87-8 ]
-
[4-(<i>tert</i>-butoxycarbonylmethyl-carbamoyl)-2,5-dichloro-phenylsulfanyl]-acetic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 6 steps
1: 96 percent / Jones reagent / acetone / 1 h / 20 °C
2: 70 percent / H2SO4 conc. / dioxane / 19 h / -78 °C
3: 81 percent / dimethylformamide / 0.83 h / 20 °C
4: 92 percent / CF3CO2H / CH2Cl2 / 4 h / 20 °C
5: 49 percent / dicyclohexylcarbodiimide / CH2Cl2 / 2 h / 20 °C
6: 94 percent / aq. NaOH / tetrahydrofuran / 0.33 h / 20 °C |
|
- 24
-
[ 35696-87-8 ]
-
[ 528839-32-9 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 6 steps
1: 96 percent / Jones reagent / acetone / 1 h / 20 °C
2: 70 percent / H2SO4 conc. / dioxane / 19 h / -78 °C
3: 81 percent / dimethylformamide / 0.83 h / 20 °C
4: 72 percent / aq. NaOH / tetrahydrofuran / 1.5 h / 20 °C
5: 98 percent / dicyclohexylcarbodiimide / tetrahydrofuran / 1.5 h / 20 °C
6: 52 percent / CF3CO2H / CH2Cl2; methoxybenzene / 4.5 h |
|
- 25
-
[ 35696-87-8 ]
-
[ 528839-31-8 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: 96 percent / Jones reagent / acetone / 1 h / 20 °C
2: 70 percent / H2SO4 conc. / dioxane / 19 h / -78 °C
3: 81 percent / dimethylformamide / 0.83 h / 20 °C
4: 72 percent / aq. NaOH / tetrahydrofuran / 1.5 h / 20 °C
5: 98 percent / dicyclohexylcarbodiimide / tetrahydrofuran / 1.5 h / 20 °C |
|
- 26
-
[ 35696-87-8 ]
-
C32H35Cl2N5O6S3(2+)*2Cl(1-)
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 7 steps
1: 96 percent / Jones reagent / acetone / 1 h / 20 °C
2: 70 percent / H2SO4 conc. / dioxane / 19 h / -78 °C
3: 81 percent / dimethylformamide / 0.83 h / 20 °C
4: 72 percent / aq. NaOH / tetrahydrofuran / 1.5 h / 20 °C
5: 98 percent / dicyclohexylcarbodiimide / tetrahydrofuran / 1.5 h / 20 °C
6: 52 percent / CF3CO2H / CH2Cl2; methoxybenzene / 4.5 h
7: methanol / 1 h / 20 °C |
|
- 27
-
[ 35696-87-8 ]
-
[ 1835-89-8 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: methyl magnesium bromide; diethyl ether
2: toluene; Al2O3 / 350 °C / <760 |
|
- 28
-
[ 6639-30-1 ]
-
[ 35696-87-8 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: Cl2, PCl5
2: H2SO4 |
|
- 29
-
[ 35696-87-8 ]
-
1-Methyl-2-(2,4,5-trichloro-phenyl)-ethylamine
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: NH4OAc / acetic acid
2: LiAlH4 |
|
- 30
-
[ 35696-87-8 ]
-
[ 123-54-6 ]
-
[ 179413-70-8 ]
Yield | Reaction Conditions | Operation in experiment |
45% |
With methylamine hydrochloride In pyridine; ethyl acetate |
1 1-[5-Acetyl-4-(2,4,5-trichlorophenyl)-1,2,6-trimethyl-1,4-dihydropyridin-3-yl]ethanone STR8
EXAMPLE 1 1-[5-Acetyl-4-(2,4,5-trichlorophenyl)-1,2,6-trimethyl-1,4-dihydropyridin-3-yl]ethanone STR8 5.0 g (23.9 mmol) of 2,4,5-trichlorobenzaldehyde, 4.8 g (47.8 mmol) of acetylacetone and 1.78 g (26.3 mmol) of methylamine hydrochloride are boiled under reflux for 5 h in 4 ml of pyridine. The pyridine is then stripped off and the residue is codistilled twice with toluene. It is taken up in AcOEt and the solution is extracted with 1N aqueous HCl. Drying and concentration of the aqueous phase yields a brown oil, which is purified by flash chromatography (petroleum ether/AcOEt=5:1). The product is finally recrystallized from ether. 4.2 g of the title compound (45% of theory) are obtained. MS:385 Rf =0.65 (petroleum ether: AcOEt:=1:1) |
- 31
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[ 1778-09-2 ]
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[ 35696-87-8 ]
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C16H11Cl3OS
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
85% |
With sodium hydroxide In ethanol; water at 20℃; for 24h; |
|
- 32
-
[ 6287-38-3 ]
-
[ 35696-87-8 ]
Yield | Reaction Conditions | Operation in experiment |
92% |
With N-chloro-succinimide; palladium diacetate; silver trifluoroacetate; anthranilic acid; trifluoroacetic acid In 1,2-dichloro-ethane at 60℃; for 24h; Sealed tube; |
|
65% |
With N-chloro-succinimide; 2-hydroxyl-5-nitro-3-(trifluoromethyl)pyridine; 4-trifluoromethylphenylamine; palladium diacetate; trifluoroacetic acid In 1,2-dichloro-ethane at 80℃; for 24h; Sealed tube; |
|
56% |
With trifluorormethanesulfonic acid; palladium diacetate; 1-fluoro-2,4,6-trimethylpyridin-1-ium tetrafluoroborate; 1,2-dichloro-ethane; 2-Amino-4-chlorobenzoic acid at 110℃; for 24h; Sealed tube; |
|
8 %Spectr. |
With aminomethanesulfonic acid; palladium diacetate; 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate; 1,2-dichloro-ethane at 110℃; for 24h; Sealed tube; regioselective reaction; |
|
Reference:
[1]Liu, Xi-Hai; Park, Hojoon; Hu, Jun-Hao; Hu, Yan; Zhang, Qun-Liang; Wang, Bao-Long; Sun, Bing; Yeung, Kap-Sun; Zhang, Fang-Lin; Yu, Jin-Quan
[Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 888 - 896]
[2]Li, Feng; Zhou, Yirong; Yang, Heng; Wang, Ziqi; Yu, Qinqin; Zhang, Fang-Lin
[Organic Letters, 2019, vol. 21, # 10, p. 3692 - 3695]
[3]Chen, Xiao-Yang; Ozturk, Seyma; Sorensen, Erik J.
[Organic Letters, 2017, vol. 19, # 23, p. 6280 - 6283]
[4]Chen, Xiao-Yang; Sorensen, Erik J.
[Journal of the American Chemical Society, 2018, vol. 140, # 8, p. 2789 - 2792]
- 33
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[ 7145-82-6 ]
-
[ 33513-42-7 ]
-
[ 35696-87-8 ]
Yield | Reaction Conditions | Operation in experiment |
95% |
Stage #1: 2,4,5-trichloroiodobenzene With isopropylmagnesium halide In tetrahydrofuran at -78℃; for 0.333333h; Inert atmosphere;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78 - 23℃; Inert atmosphere; |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 34
-
[ 591-18-4 ]
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[ 35696-87-8 ]
-
(±)-(3-bromophenyl)(2,4,5-trichlorophenyl)methanol
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
89% |
Stage #1: 1-Bromo-3-iodobenzene With isopropylmagnesium halide In tetrahydrofuran at 0℃; for 0.333333h; Inert atmosphere;
Stage #2: 2,4,5-trichlorobenzaldehyde In tetrahydrofuran at 0 - 23℃; Inert atmosphere; |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 35
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[ 35696-87-8 ]
-
(difluoro(3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)methyl)phosphonic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
2.2: 80 °C / Inert atmosphere
3.1: trimethylsilyl iodide / dichloromethane / 23 °C / Sealed tube |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 36
-
[ 35696-87-8 ]
-
(difluoro(2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)methyl)phosphonic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
2.2: 80 °C / Inert atmosphere
3.1: trimethylsilyl iodide / dichloromethane / 23 °C / Sealed tube |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 37
-
[ 35696-87-8 ]
-
(fluoro-(2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)methyl)phosphonic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
2.2: 80 °C / Inert atmosphere
3.1: trimethylsilyl iodide / dichloromethane / 23 °C / Sealed tube |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 38
-
[ 35696-87-8 ]
-
(±)-(1-fluoro-1-(2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)-2-oxo-2-phenylethyl)phosphonic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
2.2: 80 °C / Inert atmosphere
3.1: N-fluorobis(benzenesulfon)imide; Selectfluor / dichloromethane / 168 h / 23 °C / Inert atmosphere; Molecular sieve
4.1: trimethylsilyl iodide / dichloromethane / 23 °C / Sealed tube |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 39
-
[ 35696-87-8 ]
-
(±)-(2-cyclohexyl-1-fluoro-1-(2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)-2-oxoethyl)phosphonic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
2.2: 80 °C / Inert atmosphere
3.1: N-fluorobis(benzenesulfon)imide; Selectfluor / dichloromethane / 168 h / 23 °C / Inert atmosphere; Molecular sieve
4.1: trimethylsilyl iodide / dichloromethane / 23 °C / Sealed tube |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 40
-
[ 35696-87-8 ]
-
(±)-(1-fluoro-1-(2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)-2-oxo-2-(piperidin-1-yl)ethyl)phosphonic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
2.2: 80 °C / Inert atmosphere
3.1: trimethylsilyl iodide / dichloromethane / 23 °C / Sealed tube |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 41
-
[ 35696-87-8 ]
-
(±)-(1-(2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)-2-oxo-2-(piperidin-1-yl)ethyl)phosphonic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere
3.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
3.2: 80 °C / Inert atmosphere
4.1: lithium diisopropyl amide / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
5.1: trimethylsilyl iodide / dichloromethane / 23 °C / Sealed tube |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 42
-
[ 35696-87-8 ]
-
(±)-(1-(2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)-2-morpholino-2-oxoethyl)phosphonic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere
3.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
3.2: 80 °C / Inert atmosphere
4.1: lithium diisopropyl amide / tetrahydrofuran / 0 °C / Inert atmosphere
5.1: trimethylsilyl iodide / dichloromethane / 23 °C / Sealed tube |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 43
-
[ 35696-87-8 ]
-
(±)-(2-(dimethylamino)-1-(2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)-2-oxoethyl)phosphonic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere
3.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
3.2: 80 °C / Inert atmosphere
4.1: lithium diisopropyl amide / tetrahydrofuran / 0 °C / Inert atmosphere
5.1: trimethylsilyl iodide / dichloromethane / 23 °C / Sealed tube |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 44
-
[ 35696-87-8 ]
-
(±)-(1-(2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)-2-(methylamino)-2-oxoethyl)phosphonic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 7 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere
3.1: potassium carbonate / ethanol; water; toluene / 1 h / Inert atmosphere
3.2: 20 h / 80 °C / Inert atmosphere
3.3: 3 h / 70 °C / Inert atmosphere
4.1: phosphorus trichloride; bromine / chlorobenzene / 4 h / 105 °C / Inert atmosphere
5.1: 1,1'-carbonyldiimidazole / dichloromethane / 0.5 h / Sealed tube
5.2: 24 h / 23 °C / Sealed tube
6.1: 2 h / 120 °C / Sealed tube
7.1: trimethylsilyl iodide / dichloromethane / 23 °C / Sealed tube |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 45
-
[ 35696-87-8 ]
-
(±)-((2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)-(morpholinosulfonyl)methyl)phosphonic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere
3.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
3.2: 80 °C / Inert atmosphere
4.1: lithium diisopropyl amide / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere
4.2: 1 h / -78 °C / Inert atmosphere
5.1: trimethylsilyl iodide / dichloromethane / 23 °C / Sealed tube |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 46
-
[ 35696-87-8 ]
-
(+)-(fluoro(2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)(morpholinosulfonyl)methyl)phosphonic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 7 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere
3.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
3.2: 80 °C / Inert atmosphere
4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
4.2: -78 - 23 °C / Inert atmosphere
5.1: lithium diisopropyl amide / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere
5.2: -78 - 0 °C / Inert atmosphere
6.1: ChiralPak AD-H column (2 cm × 25 cm) / ethanol / Resolution of racemate
7.1: trimethylsilyl iodide / dichloromethane / 23 °C / Sealed tube |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 47
-
[ 35696-87-8 ]
-
(-)-(fluoro(2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)(morpholinosulfonyl)methyl)phosphonic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 7 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere
3.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
3.2: 80 °C / Inert atmosphere
4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
4.2: -78 - 23 °C / Inert atmosphere
5.1: lithium diisopropyl amide / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere
5.2: -78 - 0 °C / Inert atmosphere
6.1: ChiralPak AD-H column (2 cm × 25 cm) / ethanol / Resolution of racemate
7.1: trimethylsilyl iodide / dichloromethane / 23 °C / Sealed tube |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 48
-
[ 35696-87-8 ]
-
(±)-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-(2,4,5-trichlorophenyl)methanol
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: isopropylmagnesium halide / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere
1.2: 0 - 23 °C / Inert atmosphere
2.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 65 °C / Inert atmosphere |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 49
-
[ 35696-87-8 ]
-
(±)-diethyl (difluoro(3'-(hydroxy(2,4,5-trichlorophenyl)methyl)-[1,1'-biphenyl]-4-yl)methyl)phosphonate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
2.2: 80 °C / Inert atmosphere |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 50
-
[ 35696-87-8 ]
-
(±)-diethyl (difluoro(2'-fluoro-3'-(hydroxy(2,4,5-trichlorophenyl)methyl)[1,1'-biphenyl]-4-yl)methyl)phosphonate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
2.2: 80 °C / Inert atmosphere |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 51
-
[ 35696-87-8 ]
-
diethyl (fluoro(2'-fluoro-3'-(hydroxy(2,4,5-trichlorophenyl)methyl)-[1,1'-biphenyl]-4-yl)methyl)phosphonate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
2.2: 80 °C / Inert atmosphere |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 52
-
[ 35696-87-8 ]
-
(±)-(difluoro(3'-(hydroxy(2,4,5-trichlorophenyl)methyl)-[1,1'-biphenyl]-4-yl)methyl)phosphonic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: isopropylmagnesium halide / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere
1.2: 0 - 23 °C / Inert atmosphere
2.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 65 °C / Inert atmosphere
3.1: sodium carbonate / 1,2-dimethoxyethane; ethanol; water / Inert atmosphere
3.2: 80 °C / Inert atmosphere |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 53
-
[ 35696-87-8 ]
-
diethyl (1-(2'-fluoro-3'-(hydroxy(2,4,5-trichlorophenyl)methyl)-[1,1'-biphenyl]-4-yl)-2-oxo-2-phenylethyl)phosphonate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
2.2: 80 °C / Inert atmosphere |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 54
-
[ 35696-87-8 ]
-
diethyl (2-cyclohexyl-1-(2'-fluoro-3'-(hydroxy(2,4,5-trichlorophenyl)methyl)-[1,1'-biphenyl]-4-yl)-2-oxoethyl)phosphonate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
2.2: 80 °C / Inert atmosphere |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 55
-
[ 35696-87-8 ]
-
diethyl (1-fluoro-1-(2'-fluoro-3'-(hydroxy(2,4,5-trichlorophenyl)-methyl)-[1,1'-biphenyl]-4-yl)-2-oxo-2-phenylethyl)phosphonate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
2.2: 80 °C / Inert atmosphere
3.1: N-fluorobis(benzenesulfon)imide; Selectfluor / dichloromethane / 168 h / 23 °C / Inert atmosphere; Molecular sieve |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 56
-
[ 35696-87-8 ]
-
diethyl (2-cyclohexyl-1-fluoro-1-(2'-fluoro-3'-(hydroxy(2,4,5-trichlorophenyl)methyl)-[1,1'-biphenyl]-4-yl)-2-oxoethyl)phosphonate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
2.2: 80 °C / Inert atmosphere
3.1: N-fluorobis(benzenesulfon)imide; Selectfluor / dichloromethane / 168 h / 23 °C / Inert atmosphere; Molecular sieve |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 57
-
[ 35696-87-8 ]
-
diethyl (1-fluoro-1-(2'-fluoro-3'-(hydroxy(2,4,5-trichlorophenyl)-methyl)-[1,1'-biphenyl]-4-yl)-2-oxo-2-(piperidin-1-yl)ethyl)phosphonate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
2.2: 80 °C / Inert atmosphere |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 58
-
[ 35696-87-8 ]
-
1,2,4-trichloro-5-(2-fluoro-3-iodobenzyl)benzene
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 59
-
[ 35696-87-8 ]
-
diethyl ((2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)methyl)phosphonate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere
3.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
3.2: 80 °C / Inert atmosphere |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 60
-
[ 35696-87-8 ]
-
(±)-diethyl (1-(2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)-2-oxo-2-(piperidin-1-yl)ethyl)phosphonate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere
3.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
3.2: 80 °C / Inert atmosphere
4.1: lithium diisopropyl amide / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 61
-
[ 35696-87-8 ]
-
(±)-diethyl (1-(2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)-2-morpholino-2-oxoethyl)phosphonate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere
3.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
3.2: 80 °C / Inert atmosphere
4.1: lithium diisopropyl amide / tetrahydrofuran / 0 °C / Inert atmosphere |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 62
-
[ 35696-87-8 ]
-
(±)-diethyl (2-(dimethylamino)-1-(2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)-2-oxoethyl)phosphonate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere
3.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
3.2: 80 °C / Inert atmosphere
4.1: lithium diisopropyl amide / tetrahydrofuran / 0 °C / Inert atmosphere |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 63
-
[ 35696-87-8 ]
-
methyl 2-(2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)acetate
[ No CAS ]
-
ethyl 2-(2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)acetate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere
3.1: potassium carbonate / water; toluene / 1 h / Inert atmosphere
3.2: 20 h / 80 °C / Inert atmosphere |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 64
-
[ 35696-87-8 ]
-
2-(2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)acetic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere
3.1: potassium carbonate / ethanol; water; toluene / 1 h / Inert atmosphere
3.2: 20 h / 80 °C / Inert atmosphere
3.3: 3 h / 70 °C / Inert atmosphere |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 65
-
[ 35696-87-8 ]
-
2-bromo-2-(3'-(bromo(2,4,5-trichlorophenyl)methyl)-2'-fluoro-[1,1'-biphenyl]-4-yl)acetic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere
3.1: potassium carbonate / ethanol; water; toluene / 1 h / Inert atmosphere
3.2: 20 h / 80 °C / Inert atmosphere
3.3: 3 h / 70 °C / Inert atmosphere
4.1: phosphorus trichloride; bromine / chlorobenzene / 4 h / 105 °C / Inert atmosphere |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 66
-
[ 35696-87-8 ]
-
2-bromo-2-(3'-(bromo(2,4,5-trichlorophenyl)methyl)-2'-fluoro-[1,1'-biphenyl]-4-yl)-N-methylacetamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere
3.1: potassium carbonate / ethanol; water; toluene / 1 h / Inert atmosphere
3.2: 20 h / 80 °C / Inert atmosphere
3.3: 3 h / 70 °C / Inert atmosphere
4.1: phosphorus trichloride; bromine / chlorobenzene / 4 h / 105 °C / Inert atmosphere
5.1: 1,1'-carbonyldiimidazole / dichloromethane / 0.5 h / Sealed tube
5.2: 24 h / 23 °C / Sealed tube |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 67
-
[ 35696-87-8 ]
-
diethyl (1-(3'-(bromo(2,4,5-trichlorophenyl)methyl)-2'-fluoro-[1,1'-biphenyl]-4-yl)-2-(methylamino)-2-oxoethyl)phosphonate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 6 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere
3.1: potassium carbonate / ethanol; water; toluene / 1 h / Inert atmosphere
3.2: 20 h / 80 °C / Inert atmosphere
3.3: 3 h / 70 °C / Inert atmosphere
4.1: phosphorus trichloride; bromine / chlorobenzene / 4 h / 105 °C / Inert atmosphere
5.1: 1,1'-carbonyldiimidazole / dichloromethane / 0.5 h / Sealed tube
5.2: 24 h / 23 °C / Sealed tube
6.1: 2 h / 120 °C / Sealed tube |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 68
-
[ 35696-87-8 ]
-
4-(((2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)methyl)sulfonyl)morpholine
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere
3.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
3.2: 80 °C / Inert atmosphere |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 69
-
[ 35696-87-8 ]
-
(±)-diethyl ((2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)(morpholinosulfonyl)methyl)phosphonate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere
3.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
3.2: 80 °C / Inert atmosphere
4.1: lithium diisopropyl amide / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere
4.2: 1 h / -78 °C / Inert atmosphere |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 70
-
[ 35696-87-8 ]
-
(±)-4-((fluoro(2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)methyl)sulfonyl)morpholine
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere
3.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
3.2: 80 °C / Inert atmosphere
4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
4.2: -78 - 23 °C / Inert atmosphere |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 71
-
[ 35696-87-8 ]
-
(±)-diethyl (fluoro(2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)(morpholinosulfonyl)methyl)phosphonate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere
3.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
3.2: 80 °C / Inert atmosphere
4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
4.2: -78 - 23 °C / Inert atmosphere
5.1: lithium diisopropyl amide / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere
5.2: -78 - 0 °C / Inert atmosphere |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 72
-
[ 35696-87-8 ]
-
(+)-diethyl (fluoro(2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)(morpholinosulfonyl)methyl)phosphonate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 6 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere
3.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
3.2: 80 °C / Inert atmosphere
4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
4.2: -78 - 23 °C / Inert atmosphere
5.1: lithium diisopropyl amide / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere
5.2: -78 - 0 °C / Inert atmosphere
6.1: ChiralPak AD-H column (2 cm × 25 cm) / ethanol / Resolution of racemate |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 73
-
[ 35696-87-8 ]
-
(-)-diethyl (fluoro(2'-fluoro-3'-(2,4,5-trichlorobenzyl)-[1,1'-biphenyl]-4-yl)(morpholinosulfonyl)methyl)phosphonate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 6 steps
1.1: isopropylmagnesium chloride / tetrahydrofuran / -20 °C / Inert atmosphere
1.2: -20 - 23 °C / Inert atmosphere
2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 40 °C / Inert atmosphere
3.1: potassium carbonate / ethanol; water; toluene / Inert atmosphere
3.2: 80 °C / Inert atmosphere
4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
4.2: -78 - 23 °C / Inert atmosphere
5.1: lithium diisopropyl amide / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere
5.2: -78 - 0 °C / Inert atmosphere
6.1: ChiralPak AD-H column (2 cm × 25 cm) / ethanol / Resolution of racemate |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 74
-
[ 35696-87-8 ]
-
[ 626-00-6 ]
-
(±)-(3-iodophenyl)(2,4,5-trichlorophenyl)methanol
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
78% |
Stage #1: 1,3-Diiodobenzene With isopropylmagnesium chloride In tetrahydrofuran at -20℃; Inert atmosphere;
Stage #2: 2,4,5-trichlorobenzaldehyde In tetrahydrofuran at -20 - 23℃; Inert atmosphere; |
|
Reference:
[1]Witten, Michael R.; Wissler, Lisa; Snow, Melanie; Geschwindner, Stefan; Read, Jon A.; Brandon, Nicholas J.; Nairn, Angus C.; Lombroso, Paul J.; Käck, Helena; Ellman, Jonathan A.
[Journal of Medicinal Chemistry, 2017, vol. 60, # 22, p. 9299 - 9319]
- 75
-
[ 35696-87-8 ]
-
[ 501433-04-1 ]
-
(±)-(2-fluoro-3-iodophenyl)(2,4,5-trichlorophenyl)methanol
[ No CAS ]
- 76
-
[ 6287-38-3 ]
-
[ 35696-87-8 ]
-
[ 1217800-70-8 ]
Yield | Reaction Conditions | Operation in experiment |
1: 69%
2: 14 %Spectr. |
With 4-aminobenzene-1,3-disulfonic acid; palladium diacetate; 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate; 1,2-dichloro-ethane at 110℃; for 24h; Sealed tube; regioselective reaction; |
|
1: 18 %Spectr.
2: 10 %Spectr. |
With 6-amino-4-chloro-meta-toluenesulfonic acid; palladium diacetate; 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate; 1,2-dichloro-ethane at 110℃; for 24h; Sealed tube; regioselective reaction; |
|
Reference:
[1]Chen, Xiao-Yang; Sorensen, Erik J.
[Journal of the American Chemical Society, 2018, vol. 140, # 8, p. 2789 - 2792]
[2]Chen, Xiao-Yang; Sorensen, Erik J.
[Journal of the American Chemical Society, 2018, vol. 140, # 8, p. 2789 - 2792]
- 77
-
[ 35696-87-8 ]
-
N-(2,4,5-trichlorobenzyl)-1,1,1-trifluoromethanesulfonamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: borane-THF / tetrahydrofuran / 3 h / 0 °C
2: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 16 h / 0 - 20 °C
3: triphenylphosphine; water / tetrahydrofuran / 18 h / 20 °C
4: triethylamine / dichloromethane / 18 h / -78 - 20 °C |
|
- 78
-
[ 35696-87-8 ]
-
N-((4,6-dichloro-4'-methoxy-[1,1'-biphenyl]-3-yl)methyl)-1,1,1-trifluoromethanesulfonamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: borane-THF / tetrahydrofuran / 3 h / 0 °C
2: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 16 h / 0 - 20 °C
3: triphenylphosphine; water / tetrahydrofuran / 18 h / 20 °C
4: triethylamine / dichloromethane / 18 h / -78 - 20 °C
5: C26H34O5PS(1-)*Na(1+); palladium diacetate; rubidium carbonate / water; tetrahydrofuran / 16 h / 60 °C / Inert atmosphere |
|
- 79
-
[ 35696-87-8 ]
-
ethyl 2',4' -dichloro-5'-(((trifluoromethyl)sulfonamido)methyl)-[1,1'-biphenyl]-4-carboxylate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: borane-THF / tetrahydrofuran / 3 h / 0 °C
2: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 16 h / 0 - 20 °C
3: triphenylphosphine; water / tetrahydrofuran / 18 h / 20 °C
4: triethylamine / dichloromethane / 18 h / -78 - 20 °C
5: C26H34O5PS(1-)*Na(1+); palladium diacetate; rubidium carbonate / water; tetrahydrofuran / 16 h / 60 °C / Inert atmosphere |
|
- 80
-
[ 35696-87-8 ]
-
N-(2,4-dichloro-5-(6-methoxypyridin-3-yl)benzyl)-1,1,1-trifluoromethanesulfonamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: borane-THF / tetrahydrofuran / 3 h / 0 °C
2: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 16 h / 0 - 20 °C
3: triphenylphosphine; water / tetrahydrofuran / 18 h / 20 °C
4: triethylamine / dichloromethane / 18 h / -78 - 20 °C
5: C26H34O5PS(1-)*Na(1+); palladium diacetate; rubidium carbonate / water; tetrahydrofuran / 16 h / 60 °C / Inert atmosphere |
|
- 81
-
[ 35696-87-8 ]
-
N-(2,4-dichloro-5-((4-methoxyphenyl)amino)benzyl)-1,1,1-trifluoromethanesulfonamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: borane-THF / tetrahydrofuran / 3 h / 0 °C
2: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 16 h / 0 - 20 °C
3: triphenylphosphine; water / tetrahydrofuran / 18 h / 20 °C
4: triethylamine / dichloromethane / 18 h / -78 - 20 °C
5: tris-(dibenzylideneacetone)dipalladium(0); C26H34O5PS(1-)*Na(1+); rubidium carbonate / tetrahydrofuran / 16 h / 60 °C / Inert atmosphere |
|
- 82
-
[ 35696-87-8 ]
-
[ 19010-52-7 ]
Yield | Reaction Conditions | Operation in experiment |
73% |
With borane-THF In tetrahydrofuran at 0℃; for 3h; |
|
- 83
-
[ 35696-87-8 ]
-
1-(azidomethyl)-2,4,5-trichlorobenzene
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: borane-THF / tetrahydrofuran / 3 h / 0 °C
2: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 16 h / 0 - 20 °C |
|
- 84
-
[ 35696-87-8 ]
-
[ 2903-49-3 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: borane-THF / tetrahydrofuran / 3 h / 0 °C
2: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 16 h / 0 - 20 °C
3: triphenylphosphine; water / tetrahydrofuran / 18 h / 20 °C |
|
- 85
-
[ 35696-87-8 ]
-
ethyl 5'-chloro-4''-methoxy-2'-(((trifluoromethyl)sulfonamido)methyl)-[1,1':4',1''-terphenyl]-4-carboxylate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 6 steps
1: borane-THF / tetrahydrofuran / 3 h / 0 °C
2: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 16 h / 0 - 20 °C
3: triphenylphosphine; water / tetrahydrofuran / 18 h / 20 °C
4: triethylamine / dichloromethane / 18 h / -78 - 20 °C
5: C26H34O5PS(1-)*Na(1+); palladium diacetate; rubidium carbonate / water; tetrahydrofuran / 16 h / 60 °C / Inert atmosphere
6: palladium diacetate; rubidium carbonate; sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐4‐sulfonate / water; tetrahydrofuran / 16 h / 60 °C / Inert atmosphere |
|