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[ CAS No. 53903-49-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

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3d Animation Molecule Structure of 53903-49-4

Chemical Structure| 53903-49-4

Chemical Structure| 53903-49-4

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Quality Control of [ 53903-49-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 53903-49-4 ]

CAS No. :	53903-49-4	MDL No. :	MFCD04972660
Formula :	C₈H₈F₃NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BTRQZDUCUGJMPS-UHFFFAOYSA-N
M.W :	191.15	Pubchem ID :	22601721
Synonyms :

Calculated chemistry of [ 53903-49-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	42.34
TPSA :	35.25 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.85
Log Po/w (XLOGP3) :	1.75
Log Po/w (WLOGP) :	3.46
Log Po/w (MLOGP) :	2.22
Log Po/w (SILICOS-IT) :	2.13
Consensus Log Po/w :	2.28

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.34
Solubility :	0.879 mg/ml ; 0.0046 mol/l
Class :	Soluble
Log S (Ali) :	-2.11
Solubility :	1.49 mg/ml ; 0.00781 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.06
Solubility :	0.168 mg/ml ; 0.000881 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.33

Safety of [ 53903-49-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 53903-49-4 ]

* 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 [ 53903-49-4 ]
Downstream synthetic route of [ 53903-49-4 ]

[ 53903-49-4 ] Synthesis Path-Upstream 1~5

1
[ 344-39-8 ]
[ 53903-49-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With nitrogen; hydrogen In ethanol	(b) 4-Methoxy-2-(α,α,α-trifluoromethyl)aniline prepared by aminating 4-methoxy-2-(α,α,α-trifluoromethyl)nitrobenzene as follows: In a 300 ml stainless steel autoclave was placed a solution of 25.0 g (0.11 mole) of 4-methoxy-2-(α,α, α-trifluoromethyl)nitrobenzene in 150 ml of 95percent ethanol. After flushing with nitrogen, 1.1 g of 5percent palladium on carbon was added and the autoclave sealed. After flushing with nitrogen, the reactor was charged with 60 psi (413 kPa) of hydrogen and stirred. Gas uptake began immediately and the temperature was maintained between 25° C. and 30° C. by occasional cooling with an ice bath. After approximately ninety minutes, the gas uptake had ceased. The autoclave was vented, flushed with nitrogen and opened. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to afford 22 g (100percent yield) of a light yellow oil which was shown to be 4-methoxy-2-(α,α,α-trifluoromethyl)aniline. ¹ H NMR analysis indicated: (δ, CDClz) 7.82 (dd, J= 2 and 9 Hz, 1H), 7.00 (d, J=2 Hz, 1H), 6.48 (d, J=9 Hz, 1H), 3.87 (br s, 2H) and 3.60 (s, 3H). Mass spectrum analysis indicated: (m/e) 191 (M+), 176, 156, 128 and 52. It was used directly in the next step without purification.
99%	With palladium 10% on activated carbon; hydrogen In methanol; water; ethyl acetate at 20℃;	4-methoxy-1-nitro-2-(trifluoromethyl)benzene (9.0 g, 40.7 mmol)Soluble in ethyl acetate (50 mL) and methanol (100 mL),Add 10percent palladium on carbon (1.2g, 50percent water),With hydrogen balloon,Stir at room temperature overnight.Filter after the reaction,The filtrate was concentrated under reduced pressure to give a yellow oil (7.7 g, 99.0percent).Used directly for the next step.

Reference： [1] Patent: US4879398, 1989, A,
[2] Patent: CN107793413, 2018, A, . Location in patent: Paragraph 0150; 0151; 0154; 0155
[3] Tetrahedron Letters, 2004, vol. 45, # 26, p. 5131 - 5133
[4] Journal of Medicinal Chemistry, 2009, vol. 52, # 7, p. 2109 - 2118
[5] Patent: WO2005/47273, 2005, A1, . Location in patent: Page/Page column 44
[6] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 3, p. 1263 - 1268
[7] Patent: WO2012/110860, 2012, A1, . Location in patent: Page/Page column 46

2
[ 887144-94-7 ]
[ 104-94-9 ]
[ 53903-49-4 ]

Yield	Reaction Conditions	Operation in experiment
65%	With tris[2-phenylpyridinato-C₂,N]iridium(III) In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Irradiation	Under nitrogen or argon, 4-methoxy-aniline 0.4 mmol,0.2 mmol, Ir (ppy) 3(2mg) were added to the reaction and DMF1 ml flask, andthen the blue LED lights (7W) irradiation conditions at room temperature until completeconversion of trivalent iodine reagent completion of the reaction. Add 10 ml ofsaturated Na 2CO 3Aqueous solution, and extracted three times with ethyl acetate, theorganic layer was washed with water and once with saturated brine, dried over anhydrousNa 2SO 4The organic layer was dried. Column chromatography (eluent: petroleum ether 60-90: ethyl acetate = 15: 1-8: 1) to give the product in 65percent yield.
57%	With potassium carbonate; nickel(II) hydroxide In dimethyl sulfoxide at 35℃; for 2 h;	Trifluoromethyl preparation of aromatic amines of the embodiment according to the present embodiment, the aromatic amine is p-anisidine, and other reactions after the same procedures as in Example 28 treatment. The preparation method of the trifluoromethyl aromatic amine of the present embodiment, the aromatic amine is aniline, and the nickel compound is nickel hydroxide.The base is potassium carbonate, and the reaction process parameters are: 1-trifluoromethyl-1,2-phenyliodo-3(H)-one (0.5 mmol, 1.0 eq).Aromatic amine (1.5 mmol, 3.0 eq), nickel hydroxide 10 molpercent, potassium carbonate (1.5 mmol, 3.0 eq),DMSO (2 mL) was reacted at 35 ° C for 2 h, and the other reactions and workup procedures were the same as in Example 1.

Reference： [1] Patent: CN103553857, 2016, B, . Location in patent: Paragraph 0029-0030
[2] Organic Letters, 2018, vol. 20, # 13, p. 3732 - 3735
[3] Patent: CN108503552, 2018, A, . Location in patent: Paragraph 0110-0114
[4] Organic Letters, 2014, vol. 16, # 6, p. 1768 - 1771

3
[ 88-30-2 ]
[ 53903-49-4 ]

Reference： [1] Tetrahedron Letters, 2004, vol. 45, # 26, p. 5131 - 5133
[2] Patent: WO2012/110860, 2012, A1,

4
[ 98-17-9 ]
[ 53903-49-4 ]

Reference： [1] Tetrahedron Letters, 2004, vol. 45, # 26, p. 5131 - 5133

5
[ 118-83-2 ]
[ 53903-49-4 ]

Reference： [1] Patent: CN107793413, 2018, A,

[ 53903-49-4 ] Synthesis Path-Downstream 1~43

1
[ 53903-49-4 ]
[ 18906-41-7 ]

Reference： [1]Patent: FR1481052,1967,
Chem.Abstr.,1968,vol. 69

3
[ 26260-02-6 ]
[ 53903-49-4 ]
[1-(2-Iodo-phenyl)-meth-(E)-ylidene]-(4-methoxy-2-trifluoromethyl-phenyl)-amine [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5131 - 5133

4
[ 344-39-8 ]
[ 53903-49-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With nitrogen; hydrogen;palladium; In ethanol;	(b) 4-Methoxy-2-(alpha,alpha,alpha-trifluoromethyl)aniline prepared by aminating 4-methoxy-2-(alpha,alpha,alpha-trifluoromethyl)nitrobenzene as follows: In a 300 ml stainless steel autoclave was placed a solution of 25.0 g (0.11 mole) of 4-methoxy-2-(alpha,alpha, alpha-trifluoromethyl)nitrobenzene in 150 ml of 95% ethanol. After flushing with nitrogen, 1.1 g of 5% palladium on carbon was added and the autoclave sealed. After flushing with nitrogen, the reactor was charged with 60 psi (413 kPa) of hydrogen and stirred. Gas uptake began immediately and the temperature was maintained between 25 C. and 30 C. by occasional cooling with an ice bath. After approximately ninety minutes, the gas uptake had ceased. The autoclave was vented, flushed with nitrogen and opened. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to afford 22 g (100% yield) of a light yellow oil which was shown to be 4-methoxy-2-(alpha,alpha,alpha-trifluoromethyl)aniline. 1 H NMR analysis indicated: (delta, CDClz) 7.82 (dd, J= 2 and 9 Hz, 1H), 7.00 (d, J=2 Hz, 1H), 6.48 (d, J=9 Hz, 1H), 3.87 (br s, 2H) and 3.60 (s, 3H). Mass spectrum analysis indicated: (m/e) 191 (M+), 176, 156, 128 and 52. It was used directly in the next step without purification.
99%	With palladium 10% on activated carbon; hydrogen; In methanol; water; ethyl acetate; at 20℃;	4-methoxy-1-nitro-2-(trifluoromethyl)benzene (9.0 g, 40.7 mmol)Soluble in ethyl acetate (50 mL) and methanol (100 mL),Add 10% palladium on carbon (1.2g, 50% water),With hydrogen balloon,Stir at room temperature overnight.Filter after the reaction,The filtrate was concentrated under reduced pressure to give a yellow oil (7.7 g, 99.0%).Used directly for the next step.
	With hydrogen;5%-palladium/activated carbon; In ethanol; at 20℃; for 2.5h;	4-Methoxy-2-trifluoromethylaniline; A mixture of 4-methoxy-1-nitro-2-trifluoromethyl-benzene (4.9 g, 22.2 mmol) and 5% palladium on carbon (210 mg) in EtOH (28 mL) is stirred for 2.5 h at RT, under a hydrogen atmosphere. The resulting suspension is filtered through a pad of celite. The filtrate is concentrated in vacuo to afford the title compound: ES-MS: 192.0 [M] + ; single peak at tR= 3.55 min (System 2)

With hydrazine hydrate;raney Ni; In methanol; at 20℃;

Step-2:-Preperation of 4-methoxy-2-trifluoromethyl-phenylamine:-To a solution of 4-methoxy- 1 -nitro-2-trifluoromethyl-benzene (1.0 g, 4.52 mmol) in methanol (5-7 mL) was drop wise added raney Ni (cat. amount) and hydrazine hydrate (1 mL). The reaction mass was stirred at RT for 2-3 hours. The reaction mass was quenched in water and the filtrate was concentrated to afford 0.400 g of desired product. 'HNMR (DMSO- 6): delta 3.67 (s, 3H), 5.09 (s, 2H), 6.79-6.85 (m, 2H), 6.96 (d, / = 6.9 Hz, 1H).

Reference： [1]Patent: US4879398,1989,A
[2]Patent: CN107793413,2018,A .Location in patent: Paragraph 0150; 0151; 0154; 0155
[3]Tetrahedron Letters,2004,vol. 45,p. 5131 - 5133
[4]Journal of Medicinal Chemistry,2009,vol. 52,p. 2109 - 2118
[5]Patent: WO2005/47273,2005,A1 .Location in patent: Page/Page column 44
[6]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1263 - 1268
[7]Patent: WO2012/110860,2012,A1 .Location in patent: Page/Page column 46

5
[ 53903-49-4 ]
[ 104-87-0 ]
(4-Methoxy-2-trifluoromethyl-phenyl)-[1-p-tolyl-meth-(E)-ylidene]-amine [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5131 - 5133

6
[ 53903-49-4 ]
[ 104-88-1 ]
[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-(4-methoxy-2-trifluoromethyl-phenyl)-amine [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5131 - 5133

7
[ 53903-49-4 ]
[ 89-98-5 ]
[1-(2-Chloro-phenyl)-meth-(E)-ylidene]-(4-methoxy-2-trifluoromethyl-phenyl)-amine [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5131 - 5133

8
[ 53903-49-4 ]
[ 100-52-7 ]
benzylidene(4-methoxy-2-trifluoromethyl)aniline [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5131 - 5133

9
[ 53903-49-4 ]
[ 123-11-5 ]
[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-(4-methoxy-2-trifluoromethyl-phenyl)-amine [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5131 - 5133

10
[ 53903-49-4 ]
[ 630-19-3 ]
[2,2-Dimethyl-prop-(E)-ylidene]-(4-methoxy-2-trifluoromethyl-phenyl)-amine [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5131 - 5133

11
[ 53903-49-4 ]
[ 6630-33-7 ]
[1-(2-Bromo-phenyl)-meth-(E)-ylidene]-(4-methoxy-2-trifluoromethyl-phenyl)-amine [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5131 - 5133

12
[ 98-17-9 ]
[ 53903-49-4 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5131 - 5133

13
[ 88-30-2 ]
[ 53903-49-4 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5131 - 5133
[2]Patent: WO2012/110860,2012,A1

14
[ 53903-49-4 ]
(E)-5-(4-Methoxy-2-trifluoromethyl-phenylamino)-2,6,6-trimethyl-hept-2-enal [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5131 - 5133

15
[ 53903-49-4 ]
N-(4-methoxy-2-trifluoromethylphenyl)-5-amino-2-methyl-5-phenylpent-2-en-1-al [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5131 - 5133

16
[ 53903-49-4 ]
N-(4-methoxy-2-trifluoromethylphenyl)-5-amino-2-ethyl-5-phenylpent-2-en-1-al [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5131 - 5133

17
[ 53903-49-4 ]
(E)-6-(4-Methoxy-2-trifluoromethyl-phenylamino)-3-methyl-6-phenyl-hex-3-en-2-one [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5131 - 5133

18
[ 53903-49-4 ]
5-(4-methoxy-2-trifluoromethyl-phenylamino)-2-methyl-5-<i>p</i>-tolyl-pent-2-enal [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5131 - 5133

19
[ 53903-49-4 ]
(E)-5-(4-Methoxy-2-trifluoromethyl-phenylamino)-2-methyl-5-phenyl-pent-2-en-1-ol [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5131 - 5133

20
[ 53903-49-4 ]
(E)-5-(4-Chloro-phenyl)-5-(4-methoxy-2-trifluoromethyl-phenylamino)-2-methyl-pent-2-enal [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5131 - 5133

21
[ 53903-49-4 ]
(E)-5-(4-Methoxy-phenyl)-5-(4-methoxy-2-trifluoromethyl-phenylamino)-2-methyl-pent-2-enal [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5131 - 5133

22
[ 53903-49-4 ]
(E)-5-(2-Bromo-phenyl)-5-(4-methoxy-2-trifluoromethyl-phenylamino)-2-methyl-pent-2-enal [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5131 - 5133

23
[ 53903-49-4 ]
(E)-5-(2-Chloro-phenyl)-5-(4-methoxy-2-trifluoromethyl-phenylamino)-2-methyl-pent-2-enal [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5131 - 5133

24
[ 53903-49-4 ]
(E)-5-(2-Iodo-phenyl)-5-(4-methoxy-2-trifluoromethyl-phenylamino)-2-methyl-pent-2-enal [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5131 - 5133

25
[ 123-56-8 ]
[ 75-18-3 ]
[ 53903-49-4 ]
[ 107-06-2 ]
[ 126312-64-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium hydroxide; N-chloro-succinimide; In dichloromethane;	(c) 4-Methoxy-6-(methylthiomethyl)-2-(alpha,alpha,alpha-trifluoromethyl)aniline was prepared by substituting 4-methoxy-2-(alpha,alpha,alpha-trifluoromethyl)aniline as follows: In a 250 ml three-necked flask equipped with an overhead stirrer was placed 20.12 g (0.105 mol) of 4-methoxy-2-(alpha,alpha,alpha-trifluoromethyl)aniline in 100 ml of methylene chloride. To the solution was then added 15.63 g (0.117 mol) of N-chlorosuccinimide was added with vigorous stirring. After cooling to 0 C. under a nitrogen atmosphere, a solution of 9.2 ml (8.02 g, 0.129 mol) dimethylsulfide in 40 ml of methylene chloride was then added over a one hour period while maintaining the temperature below 5 C. The reaction mixture became very thick. The ice bath was removed and after stirring at room temperature for one hour, 200 ml of ice cold 5% aqueous sodium hydroxide solution was added. The methylene chloride layer was separated, dried over anhydrous potassium carbonate, filtered and the solvent removed under reduced pressure. To the residue was then added 60 ml of 1,2-dichloroethane and 1.00 g (10 mmol) of succinimide. After refluxing for twelve hours under a nitrogen atmosphere, the reaction mixture was cooled, washed twice with 100 ml of 5% sodium hydroxide solution, dried with magnesium sulfate, filtered and concentrated under reduced pressure to afford 24.9 g of a black oil. This was distilled under reduced pressure to afford 16.5 g (63% yield) of the desired product as a clear, colorless liquid (Bp 106-110 at 0.35 mm Hg) of 95% purity as assayed by gas chromatography; 1 H NMR analysis indicated: (delta, CDCl3) 6.94 (d, J=1.8 Hz, 1H), 6.78 (d, J=1.8 Hz, 1H), 4.32 (br s, 2H, NHz), 3.54 (s, 3H), 3.51 (s, 2H) and 1.82 (s, 3H). Mass spectrum analysis indicated: (m/e) 251 (M+), 204 (100%) and 181.

Reference： [1]Patent: US4879398,1989,A

26
[ 53903-49-4 ]
[ 372-31-6 ]
[ 35853-42-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1263 - 1268
[2]Journal of Medicinal Chemistry,2009,vol. 52,p. 2109 - 2118

27
[ 53903-49-4 ]
[ 105942-08-3 ]
[ 1360431-01-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium phosphate;tris-(dibenzylideneacetone)dipalladium(0); XPhos; In toluene; at 110℃; for 20h;Inert atmosphere;	<strong>[53903-49-4]2-Amino-5-methoxy-benzotrifluoride</strong> (10.46 mmol), K3PO4 (15.7 mmol), Xphos (1.05 mmol) and Pd4(dba)3 (0.314 mmol) were added under nitrogen to a solution of 4-bromo-2-fluoro-benzonitrile (10.46 mmol) in 50 mL toluene and the mixture was stirred for 20 hours at a bath temperature of 110 C. Then the mixture was filtered through a glass fibre filter, then the filtrate was extracted with 150 mL water. The organic phase was dried on sodium sulphate and evaporated down. In this way the product was obtained in a yield of 87% of theory. C15H10F4N2O (310.2) Mass spectrum (ESI): [M+H]+=311 [M-H]-=309 Thin layer chromatograph (silica gel; petroleum ether/ethyl acetate 7:3): Rf=0.48

Reference： [1]Patent: US2012/208823,2012,A1 .Location in patent: Page/Page column 17

28
[ 53903-49-4 ]
[ 1360431-02-2 ]

Reference： [1]Patent: US2012/208823,2012,A1

29
[ 53903-49-4 ]
[ 1360430-75-6 ]

Reference： [1]Patent: US2012/208823,2012,A1

30
[ 887144-94-7 ]
[ 104-94-9 ]
[ 53903-49-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium carbonate; In acetonitrile; at 75℃; for 6h;Schlenk technique; Inert atmosphere;	General procedure: Experimental Procedure: A dried 25 mL Schlenk tube equipped with a magnetic stir bar was charged with Togni?s Reagent 2 (0.25 mmol, 1.0 equiv), free anilines 1 (0.75 mmol, 3.0 equiv), K2CO3 (0.375 mmol, 1.5 equiv) and CH3CN (1.5 mL). The reaction mixture was then stirred at 75 C for 6 h under an argon atmosphere. The reaction progress was monitored by TLC. After cooling to room temperature, the mixture was washed with water and extracted with CH2Cl2 three times, then washed with saturated NaCl solution. The combined organic layer was dried with anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo. The crude product was purified by flash column chromatography on silica gel (Elutent: petroleum ether-EtOAc) to give the pure product. The products were characterized by 1H NMR, 13C NMR, 19F NMR, GC -MS.
65%	With tris[2-phenylpyridinato-C2,N]iridium(III); In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; Irradiation;	Under nitrogen or argon, 4-methoxy-aniline 0.4 mmol,0.2 mmol, Ir (ppy) 3(2mg) were added to the reaction and DMF1 ml flask, andthen the blue LED lights (7W) irradiation conditions at room temperature until completeconversion of trivalent iodine reagent completion of the reaction. Add 10 ml ofsaturated Na 2CO 3Aqueous solution, and extracted three times with ethyl acetate, theorganic layer was washed with water and once with saturated brine, dried over anhydrousNa 2SO 4The organic layer was dried. Column chromatography (eluent: petroleum ether 60-90: ethyl acetate = 15: 1-8: 1) to give the product in 65% yield.
57%	With potassium carbonate; nickel(II) hydroxide; In dimethyl sulfoxide; at 35℃; for 2h;	Trifluoromethyl preparation of aromatic amines of the embodiment according to the present embodiment, the aromatic amine is p-anisidine, and other reactions after the same procedures as in Example 28 treatment. The preparation method of the trifluoromethyl aromatic amine of the present embodiment, the aromatic amine is aniline, and the nickel compound is nickel hydroxide.The base is potassium carbonate, and the reaction process parameters are: 1-trifluoromethyl-1,2-phenyliodo-3(H)-one (0.5 mmol, 1.0 eq).Aromatic amine (1.5 mmol, 3.0 eq), nickel hydroxide 10 mol%, potassium carbonate (1.5 mmol, 3.0 eq),DMSO (2 mL) was reacted at 35 C for 2 h, and the other reactions and workup procedures were the same as in Example 1.

Reference： [1]Tetrahedron Letters,2020,vol. 61
[2]Patent: CN103553857,2016,B .Location in patent: Paragraph 0029-0030
[3]Organic Letters,2018,vol. 20,p. 3732 - 3735
[4]Patent: CN108503552,2018,A .Location in patent: Paragraph 0110-0114
[5]Organic Letters,2014,vol. 16,p. 1768 - 1771

31
[ 119072-55-8 ]
[ 53903-49-4 ]
[ 104-87-0 ]
[ 637-44-5 ]
C₃₀H₂₉F₃N₂O₃ [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 1040 - 1043

32
[ 53903-49-4 ]
4,4-difluoro-4-(2-fluorodimethylsilyl-5-methoxyphenyl)-1-butene [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 10406 - 10409
Angew. Chem.,2016,vol. 128,p. 10562 - 10565,4

33
[ 53903-49-4 ]
2-diphenylsilyl-5-methoxybenzotrifluoride [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 10406 - 10409
Angew. Chem.,2016,vol. 128,p. 10562 - 10565,4

34
[ 53903-49-4 ]
4,4-difluoro-4-(2-fluorodiphenylsilyl-5-methoxyphenyl)-1-butene [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 10406 - 10409
Angew. Chem.,2016,vol. 128,p. 10562 - 10565,4

35
[ 53903-49-4 ]
2-dimethylsilyl-5-methoxybenzotrifluoride [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 10406 - 10409
Angew. Chem.,2016,vol. 128,p. 10562 - 10565,4

36
[ 53903-49-4 ]
[ 1261645-09-3 ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 10406 - 10409
Angew. Chem.,2016,vol. 128,p. 10562 - 10565,4

37
[ 53903-49-4 ]
N-[4-methoxy-5-nitro-2-(trifluoromethyl)phenyl]acetamide [ No CAS ]

Reference： [1]Patent: CN107793413,2018,A

38
[ 53903-49-4 ]
N-[5-amino-4-methoxy-2-(trifluoromethyl)phenyl]acetamide [ No CAS ]

Reference： [1]Patent: CN107793413,2018,A

39
[ 53903-49-4 ]
N-(4-methoxy-5-[4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl]amino}-2-(trifluoromethyl)phenyl)acetamide [ No CAS ]

Reference： [1]Patent: CN107793413,2018,A

40
[ 53903-49-4 ]
6-methoxy-N₁-[4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl]-4-(trifluoromethyl)benzene-1,3-diamine [ No CAS ]

Reference： [1]Patent: CN107793413,2018,A

41
[ 53903-49-4 ]
N-(4-methoxy-5-(4-(1-methyl-1H-indol-3-yl)pyrimidin-2-ylamino)-2-(trifluoromethyl)phenyl)acrylamide [ No CAS ]

Reference： [1]Patent: CN107793413,2018,A

42
[ 53903-49-4 ]
[ 108-24-7 ]
[ 142955-44-0 ]

Yield	Reaction Conditions	Operation in experiment
92.3%	With triethylamine; In dichloromethane; at 20℃;	Dissolve <strong>[53903-49-4]4-methoxy-2-(trifluoromethyl)aniline</strong> (4.8 g, 25.1 mmol) in dichloromethane (10 mL),Triethylamine (5.0 g, 50.0 mmol) was addedAnd acetic anhydride (5.0 g, 50.0 mmol).The reaction solution was stirred at room temperature overnight.After the reaction was completed, water (100 mL) was added.Extract with dichloromethane (100 mL x 3).Combine the organic phase,The organic phase was washed with saturated brine (100 mL).Drying with anhydrous sodium sulfateConcentration under reduced pressure gave a grey solid.The gray solid was washed with a mixture of petroleum ether and ethyl acetate (20:1).A white solid was obtained (5.4 g, yield: 92.3%).

Reference： [1]Patent: CN107793413,2018,A .Location in patent: Paragraph 0150; 0151; 0156; 0157

43
[ 118-83-2 ]
[ 53903-49-4 ]

Reference： [1]Patent: CN107793413,2018,A

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Isomers

Technical Information

• 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Addition of an Amine to a Conjugated Enone • Acetal Formation • Acidity of Phenols • Alkyl Halide Occurrence • Amides Can Be Converted into Aldehydes • Amine Synthesis from Nitriles • Amine Synthesis from Nitriles • Amines Convert Acyl Chlorides into Amides • Amines Convert Esters into Amides • An Alkane are Prepared from an Haloalkane • Azide Reduction by LiAlH4 • Azide Reduction by LiAlH4 • Basicity of Amines • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Chichibabin Reaction • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Conjugate Additions of p-Benzoquinones • Conversion of Amino with Nitro • Decomposition of Arenediazonium Salts to Give Phenols • Deprotonation of Methylbenzene • Diazo Coupling • Diazotization Reaction • DIBAL Attack Nitriles to Give Ketones • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Electrophilic Substitution of the Phenol Aromatic Ring • Enamine Formation • Esters Are Reduced by LiAlH4 to Give Alcohols • Esters Hydrolyze to Carboxylic Acids and Alcohols • Ether Synthesis by Oxymercuration-Demercuration • Etherification Reaction of Phenolic Hydroxyl Group • Ethers Synthesis from Alcohols with Strong Acids • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation of Benzene with Haloalkanes • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Grignard Reagents Transform Esters into Alcohols • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Benzene • Halogenation of Phenols • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hofmann Elimination • Hofmann Rearrangement • Hydride Reductions • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Hydrolysis of Imines to Aldehydes and Ketones • Imine Formation from Amines and Aldehydes or Ketones • Kolbe-Schmitt Reaction • Leuckart-Wallach Reaction • Mannich Reaction • Methylation of Ammonia • Methylation of Ammonia • Nitration of Benzene • Nitrosation of Amines • Nomenclature of Ethers • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Oxidation of Phenols • Pechmann Coumarin Synthesis • Peptide Bond Formation with DCC • Petasis Reaction • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Preparation of Ethers • Preparation of LDA • Primary Ether Cleavage with Strong Nucleophilic Acids • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Ethers • Reduction of an Amide to an Amine • Reduction of an Amide to an Amine • Reductive Amination • Reductive Amination • Reductive Removal of a Diazonium Group • Reimer-Tiemann Reaction • Reverse Sulfonation——Hydrolysis • Ring Opening of Azacyclopropanes • Ring Opening of Azacyclopropanes • Ring Opening of Oxacyclobutanes • Ring Opening of Oxacyclopropane • Specialized Acylation Reagents-Vilsmeier Reagent • Strecker Synthesis • Sulfonation of Benzene • Synthesis of 2-Amino Nitriles • Synthesis of Alcohols from Tertiary Ethers • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Nitro Group Conver to the Amino Function • The Nucleophilic Opening of Oxacyclopropanes • Ugi Reaction • Vilsmeier-Haack Reaction

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