[ CAS No. 105202-02-6 ] {[proInfo.proName]}

Name: 105202-02-6|2-Iodo-5-(trifluoromethyl)aniline|95%
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SKU: A270472
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Quality Control of [ 105202-02-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 105202-02-6 ]

CAS No. :	105202-02-6	MDL No. :	MFCD04972658
Formula :	C₇H₅F₃IN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KJTQOUZTJKNWGK-UHFFFAOYSA-N
M.W :	287.02	Pubchem ID :	13571938
Synonyms :

Calculated chemistry of [ 105202-02-6 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	48.57
TPSA :	26.02 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) :	-6.08 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.21
Log Po/w (XLOGP3) :	2.78
Log Po/w (WLOGP) :	4.05
Log Po/w (MLOGP) :	3.44
Log Po/w (SILICOS-IT) :	3.1
Consensus Log Po/w :	3.12

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.67
Solubility :	0.0607 mg/ml ; 0.000211 mol/l
Class :	Soluble
Log S (Ali) :	-2.98
Solubility :	0.299 mg/ml ; 0.00104 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.87
Solubility :	0.0388 mg/ml ; 0.000135 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.73

Safety of [ 105202-02-6 ]

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

Application In Synthesis of [ 105202-02-6 ]

* 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 [ 105202-02-6 ]
Downstream synthetic route of [ 105202-02-6 ]

[ 105202-02-6 ] Synthesis Path-Upstream 1~4

1
[ 105202-02-6 ]
[ 13544-43-9 ]

Reference： [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 16, p. 3054 - 3064

2
[ 400-97-5 ]
[ 105202-02-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With iron; acetic acid In ethanol at 23℃; for 3 h;	To a solution of compound 52 (850 mg, 2.68 mmol) in HOAc- EtOH (10 mL, 1 :5, v/v) was added iron dust (750 mg, 13.43 mmol) at 23 °C. The resulting mixture was stirred at 23 °C for 3 h before it was quenched with a saturated solution of NaHC0₃ (20 mL) and diluted with EtOAc (50 mL). The layers were separated, and the organic layer was extracted with H₂0 (3 x 10 mL). The combined organic layers were dried over Na₂SO₄ and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, hexanes: EtOAc 10: 1 ) to give compound 53 (754 mg, 98percent) as a yellow solid. (0468) [00359] ¹ H NMR (400 MHz, CDCI₃) δ = 7.76 (dd, J = 8.2, 0.7 Hz, 1 H), 6.96 (d, J = 1 .7 Hz, 1 H), 6.72 (ddd, J = 8.2, 2.0, 0.6 Hz, 1 H), 4.32 (brs, 2H). m/z (ESI) 288.0 [M+H⁺].
89.5%	With ammonium chloride; iron In water	b Preparation of 2-amino-4-trifluoromethyliodobenzene: A mixture of 225 ml of water, 166 g of iron and 10.03 g of ammonium chloride are heated to reflux. 317 g of 2-nitro-4-trifluoromethyliodobenzene are added thereto over a period of 2 hours, then refluxing is continued for 3 hours 30 minutes when the addition is complete. The whole is allowed to cool then the medium is extracted 4 times with 250 ml of benzene each time. The mixture is then filtered and subsequently decanted. The organic layer is dried and the solvent is evaporated. After distillation, 256 g of 2-amino-4-trifluoromethyliodobenzene are recovered, b.p.: 102° to 114° C., ind (25° C.): 1.556. (Yield: 89.5percent).

Reference： [1] Patent: WO2016/29310, 2016, A1, . Location in patent: Paragraph 00357-00359
[2] Patent: US5079245, 1992, A,
[3] Angewandte Chemie - International Edition, 2011, vol. 50, # 32, p. 7354 - 7358
[4] Patent: US5998334, 1999, A,
[5] Organic Letters, 2017, vol. 19, # 17, p. 4484 - 4487

3
[ 400-98-6 ]
[ 105202-02-6 ]

Reference： [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 32, p. 7354 - 7358
[2] Patent: WO2016/29310, 2016, A1,
[3] Organic Letters, 2017, vol. 19, # 17, p. 4484 - 4487

4
[ 98-16-8 ]
[ 105202-02-6 ]

Reference： [1] Synthesis, 2006, # 7, p. 1183 - 1189
[2] Patent: WO2006/118155, 2006, A1, . Location in patent: Page/Page column 33

[ 105202-02-6 ] Synthesis Path-Downstream 1~88

1
[ 7357-70-2 ]
[ 105202-02-6 ]
[ 112146-11-9 ]

Reference： [1]Chemistry Letters,1987,p. 839 - 840

2
[ 105202-02-6 ]
[ 103-85-5 ]
[ 105202-01-5 ]

Reference： [1]Chemistry Letters,1986,p. 265 - 266

3
[ 55477-80-0 ]
[ 105202-02-6 ]
3-(2-amino-4-trifluoromethylphenyl)-2-tert-butoxycarbonylaminoacrylic acid methyl ester [ No CAS ]

Reference： [1]Synthesis,2006,p. 1183 - 1189

4
[ 98-16-8 ]
[ 105202-02-6 ]

Reference： [1]Synthesis,2006,p. 1183 - 1189
[2]Patent: WO2006/118155,2006,A1 .Location in patent: Page/Page column 33

5
[ 540-80-7 ]
[ 624-92-0 ]
[ 105202-02-6 ]
[ 199125-35-4 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; chloroform;	3) To a solution containing a part (5.1 g) of 3-amino-4-iodebenzotrifluoride obtained in the preceding step, 16.75 g of dimethyldisulfide and 80 ml of chloroform, a solution having the rest (20.42 g) of 3-amino-4-iodebenzotrifluoride obtained in the preceding step dissolved in 20 ml of chloroform and 11.92 g of tert-butylnitrite, were simultaneously dropwise added at a temperature of from 25 to 30 C. After completion of the dropwise addition, the mixture was reacted at room temperature for 16 hours. After completion of the reaction, 200 ml of methylene chloride was added to the reaction mixture, and the mixture was washed with an aqueous hydrochloric acid solution with pH 1 to 2. Then, the methylene chloride layer was washed with water and dried over anhydrous sodium sulfate. Then, methylene chloride and chloroform were distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 19.89 g of the desired product as an oily substance. The NMR spectrum data of this product are as follows. 1 H-NMR deltappm [Solvent: CDCl3 ] 2.51 (s,3H), 7.08 (dd,1H), 7.26 (d,1H), 7.90 (dd,1H)

Reference： [1]Patent: US5998334,1999,A

6
[ 400-97-5 ]
[ 105202-02-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With iron; acetic acid; In ethanol; at 23℃; for 3h;	To a solution of compound 52 (850 mg, 2.68 mmol) in HOAc- EtOH (10 mL, 1 :5, v/v) was added iron dust (750 mg, 13.43 mmol) at 23 C. The resulting mixture was stirred at 23 C for 3 h before it was quenched with a saturated solution of NaHC03 (20 mL) and diluted with EtOAc (50 mL). The layers were separated, and the organic layer was extracted with H20 (3 x 10 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, hexanes: EtOAc 10: 1 ) to give compound 53 (754 mg, 98%) as a yellow solid. (0468) [00359] 1 H NMR (400 MHz, CDCI3) delta = 7.76 (dd, J = 8.2, 0.7 Hz, 1 H), 6.96 (d, J = 1 .7 Hz, 1 H), 6.72 (ddd, J = 8.2, 2.0, 0.6 Hz, 1 H), 4.32 (brs, 2H). m/z (ESI) 288.0 [M+H+].
89.5%	With ammonium chloride; iron; In water;	b Preparation of 2-amino-4-trifluoromethyliodobenzene: A mixture of 225 ml of water, 166 g of iron and 10.03 g of ammonium chloride are heated to reflux. 317 g of 2-nitro-4-trifluoromethyliodobenzene are added thereto over a period of 2 hours, then refluxing is continued for 3 hours 30 minutes when the addition is complete. The whole is allowed to cool then the medium is extracted 4 times with 250 ml of benzene each time. The mixture is then filtered and subsequently decanted. The organic layer is dried and the solvent is evaporated. After distillation, 256 g of 2-amino-4-trifluoromethyliodobenzene are recovered, b.p.: 102 to 114 C., ind (25 C.): 1.556. (Yield: 89.5%).
	With iron; In acetic acid;	2) A solution having 30 g of 4-iodo-3-nitrobenzotrifluoride obtained in the preceding step dissolved in 300 ml of acetic acid, was heated, and 26.43 g of reduced iron was added thereto over a period of 15 minutes at a temperature of from 85 to 95 C. Then, the mixture was reacted for further 5 minutes at the same temperature. After completion of the reaction, the reaction mixture was cooled with ice, and insoluble matters were filtered off using celite. The filtration cake was thoroughly washed with ethyl acetate, and the washing liquid and the filtrate were mixed, followed by washing with water for 5 times. The obtained ethyl acetate layer was dried over anhydrous sodium sulfate, and ethyl acetate was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 25.52 g of oily 3-amino-4-iodobenzotrifluoride. The NMR spectrum data of this product are as follows. hu 1H-NMR deltappm [Solvent: CDCl3 ] 6.70 (dd,1H), 6.93 (d,1H), 7.73 (d,1H)

Reference： [1]Patent: WO2016/29310,2016,A1 .Location in patent: Paragraph 00357-00359
[2]Journal of Medicinal Chemistry,2019,vol. 62,p. 5049 - 5062
[3]Patent: US5079245,1992,A
[4]Angewandte Chemie - International Edition,2011,vol. 50,p. 7354 - 7358
[5]Patent: US5998334,1999,A
[6]Organic Letters,2017,vol. 19,p. 4484 - 4487

7
[ 105202-02-6 ]
[ 914642-99-2 ]

Reference： [1]Patent: WO2006/118155,2006,A1 .Location in patent: Page/Page column 34

8
4-(4-ethynylphenoxy)benzonitrile [ No CAS ]
[ 105202-02-6 ]
[ 1162684-33-4 ]

Reference： [1]Heterocycles,2009,vol. 79,p. 487 - 520

9
[ 14395-53-0 ]
[ 105202-02-6 ]
C₁₄H₁₁BrF₃NS [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 1291 - 1294

10
[ 6320-02-1 ]
[ 105202-02-6 ]
[ 328-14-3 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 1291 - 1294

11
[ 75-15-0 ]
[ 123-30-8 ]
[ 105202-02-6 ]
[ 1269795-92-7 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 1118 - 1121

12
[ 75-15-0 ]
[ 105202-02-6 ]
[ 100-53-8 ]
[ 1303996-80-6 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 4200 - 4204

13
[ 628-71-7 ]
[ 105202-02-6 ]
[ 1333392-13-4 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 7354 - 7358

14
[ 105202-02-6 ]
[ 1333391-76-6 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 7354 - 7358

15
[ 105202-02-6 ]
[ 1333392-04-3 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 7354 - 7358

16
[ 400-98-6 ]
[ 105202-02-6 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 7354 - 7358
[2]Patent: WO2016/29310,2016,A1
[3]Organic Letters,2017,vol. 19,p. 4484 - 4487
[4]Journal of Medicinal Chemistry,2019,vol. 62,p. 5049 - 5062

17
[ 105202-02-6 ]
[ 1356126-74-3 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 836 - 839

18
[ 105202-02-6 ]
[ 1066-54-2 ]
[ 684250-11-1 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 836 - 839

19
[ 105202-02-6 ]
[ 1436417-15-0 ]

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 3054 - 3064

20
[ 105202-02-6 ]
[ 13544-43-9 ]

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 3054 - 3064

21
[ 105202-02-6 ]
[ 74-86-2 ]
[ 684250-11-1 ]

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 3054 - 3064

22
[ 52670-38-9 ]
[ 105202-02-6 ]
C₁₅H₁₁F₃N₂ [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 3054 - 3064

23
[ 110-52-1 ]
[ 105202-02-6 ]
C₁₁H₁₁F₃IN [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 12307 - 12310
Angew. Chem.,2012,vol. 124,p. 12307 - 12310,4

24
[ 105202-02-6 ]
[ 1438277-69-0 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 12307 - 12310
Angew. Chem.,2012,vol. 124,p. 12307 - 12310,4

25
[ 105202-02-6 ]
[ 1438277-55-4 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 12307 - 12310
Angew. Chem.,2012,vol. 124,p. 12307 - 12310,4

26
[ 105202-02-6 ]
[ 1443006-54-9 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 12307 - 12310
Angew. Chem.,2012,vol. 124,p. 12307 - 12310,4

27
[ 105202-02-6 ]
[ 1427218-62-9 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 550 - 553

28
[ 105202-02-6 ]
C₁₉H₁₉F₃INO₃S₂ [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 550 - 553

29
[ 105202-02-6 ]
[ 1420043-09-9 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 550 - 553

30
[ 105202-02-6 ]
[ 1420042-98-3 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 550 - 553

31
[ 105202-02-6 ]
[ 98-59-9 ]
[ 1427218-64-1 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 550 - 553

32
[ 105202-02-6 ]
[ 1448535-78-1 ]

Reference： [1]Tetrahedron,2013,vol. 69,p. 7211 - 7219

33
[ 105202-02-6 ]
[ 1448535-57-6 ]

Reference： [1]Tetrahedron,2013,vol. 69,p. 7211 - 7219

34
[ 105202-02-6 ]
C₁₈H₂₇F₃INO₃Si [ No CAS ]

Reference： [1]Tetrahedron,2013,vol. 69,p. 7211 - 7219

35
[ 105202-02-6 ]
[ 1448535-62-3 ]

Reference： [1]Tetrahedron,2013,vol. 69,p. 7211 - 7219

36
[ 105202-02-6 ]
[ 1448535-71-4 ]

Reference： [1]Tetrahedron,2013,vol. 69,p. 7211 - 7219

37
[ 24424-99-5 ]
[ 105202-02-6 ]
C₁₇H₂₁F₃INO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; In tetrahydrofuran; for 6h;Reflux;	General procedure: General procedure for 5a, 5c-g: To a solution of the aniline (5.40mmol) in anhydrous THF (35mL) was added Boc2O (12.42mmol) followed by DMAP (0.54mmol). The solution was stirred at reflux for 6h then concentrated to dryness and partitioned between 0.5N-HCl (100mL) and EtOAc (100mL). The aqueous layer was extracted with EtOAc (2×50mL) and the combined organic layer was washed with brine (50mL), dried over Na2SO4, filtered, and concentrated to afford the crude di-Boc product. The crude material was dissolved in methanol (35mL), treated with potassium carbonate (16.2mmol), and stirred at reflux for 6h. The mixture was concentrated to dryness and partitioned between 0.5N-HCl (100mL) and EtOAc (100mL). The aqueous phase was extracted with EtOAc (2×50mL) and the combined organic layer was washed with brine (50mL), dried over Na2SO4, filtered, and concentrated in reduced pressure. The crude product was purified by flash silica gel column chromatography (n-hexane/EtOAc=9:1) to afford carbamate 5.

Reference： [1]Tetrahedron,2013,vol. 69,p. 7211 - 7219

38
[ 70577-95-6 ]
[ 105202-02-6 ]
C₁₂H₈F₆INO₂ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 2460 - 2467

39
[ 70577-95-6 ]
[ 105202-02-6 ]
methyl 2,6-bis(trifluoromethyl)-1H-indole-3-carboxylate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 2460 - 2467

40
[ 105202-02-6 ]
t-butyl (3-chloroprop-2-yn-1-yl)(2-iodo-5-(trifluoromethyl)phenyl)carbamate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 10249 - 10254

41
[ 105202-02-6 ]
t-butyl (E)-3-(chloromethylene)-6-(trifluoromethyl)indoline-1-carboxylate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 10249 - 10254

42
[ 105202-02-6 ]
tert-butyl (2-iodo-5-(trifluoromethyl)phenyl)(prop-2-yn-1-yl)carbamate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 10249 - 10254

43
[ 24424-99-5 ]
[ 105202-02-6 ]
[ 1448535-57-6 ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 10249 - 10254

44
[ 105202-02-6 ]
[ 365564-11-0 ]
C₂₀H₂₉F₃N₂Si [ No CAS ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 975 - 979

45
[ 105202-02-6 ]
(Z)-3-(2-amino-4-(trifluoromethyl)benzylidene)-2-methylisoindolin-1-one [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 14,p. 85 - 92

46
[ 105202-02-6 ]
[ 1066-54-2 ]
[ 467451-95-2 ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 14,p. 85 - 92

47
[ 105202-02-6 ]
[ 536-74-3 ]
[ 1181455-55-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 23℃; for 6h;	To a solution of compound 53 (620 mg, 2.16 mmol) in DMF (5 mL) was added phenylacetylene (331 mg, 356 muL, 3.24 mmol), PdCI2(PPh3)2 (76 mg, 0.108 mmol), Cul (25 mg, 0.131 mmol) and Et3N (656 mg, 903 muL, 6.48 mmol) at 23 C. The reaction mixture was stirred for 6 h at 23 C before it was quenched with a saturated solution of NH4CI (10 mL) and diluted with EtOAc (50 mL). The layers were separated, and the organic layer was extracted with H20 (3 x 10 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, hexanes:EtOAc 5: 1 ) to give compound 54 (518 mg, 92%) as pale yellow solid. (0472) [00362] 1 H NMR (400 MHz, CDCI3) delta = 7.56 (m, 2H), 7.47 (dd, J = 8.5, 0.8 Hz, 1 H), 7.42 - 7.38 (m, 3H), 6.98 - 6.96 (m, 2H), 4.48 (brs, 2H); 13C NMR (101 MHz, CDCI3) delta = 147.8, 132.5, 131 .6, 131 .5 (q, J = 32.2 Hz), 128.7, 128.5, 124.0 (q, J = 272.3 Hz), 122.6, 1 14.3 (q, J = 3.8 Hz), 1 1 1 .2, 1 10.7 (q, J = 4.0 Hz), 96.5, 84.6; 19F NMR (376 MHz, CDCI3) delta = -63.13. m/z (ESI) 262.1 [M+H+].
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; In acetonitrile;Inert atmosphere; Reflux;	General procedure: PdCl2(PPh3)2 (35.1 mg, 0.05 mmol), CuI (9.5 mg, 0.05 mmol), PPh3 (13.1 mg, 0.05 mmol) and iodoaniline derivatives (1.00 mmol) were stirred under N2 in a mixed solvent with CH3CN (5 mL) and Et3N (1 mL). The alkyne (1.20 mmol) was added to the mixture and stirred in reflux. The reaction was monitored by TLC. After completion, H2O (10 mL) was added to the reaction mixture and extracted with ethyl acetate (3 × 10 mL). The combined organic solution was washed with brine, dried over anhydrous MgSO4, concentrated at the reduced pressure. And the crude product was purified by column chromatography to give 2-alkynylanilines.

Reference： [1]Patent: WO2016/29310,2016,A1 .Location in patent: Paragraph 00360-00362
[2]Journal of Medicinal Chemistry,2019,vol. 62,p. 5049 - 5062
[3]Organic and Biomolecular Chemistry,2017,vol. 15,p. 6997 - 7007
[4]Tetrahedron Letters,2018,vol. 59,p. 3719 - 3723

48
[ 1423042-89-0 ]
[ 105202-02-6 ]
(4aS,11cR)-4a-methoxy-9-(trifluoromethyl)-1,4a,5,6,7,11c-hexahydro-2H-benzo[c]carbazol-2-one [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 1506 - 1509

49
[ 1423042-89-0 ]
[ 105202-02-6 ]
4-(4-(2-amino-4-(trifluoromethyl)phenyl)but-3-yn-1-yl)-4-methoxycyclohexa-2,5-dien-1-one [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 1506 - 1509

50
[ 105202-02-6 ]
[ 2284-20-0 ]
[ 1213706-20-7 ]

Reference： [1]Applied Organometallic Chemistry,2016,vol. 30,p. 446 - 450

51
[ 105202-02-6 ]
[ 1544-68-9 ]
[ 1370259-66-7 ]

Reference： [1]Applied Organometallic Chemistry,2016,vol. 30,p. 446 - 450

52
[ 2131-55-7 ]
[ 105202-02-6 ]
[ 1213706-19-4 ]

Reference： [1]Applied Organometallic Chemistry,2016,vol. 30,p. 446 - 450

53
[ 105202-02-6 ]
[ 2131-61-5 ]
[ 1160166-36-8 ]

Reference： [1]Applied Organometallic Chemistry,2016,vol. 30,p. 446 - 450

54
[ 103-72-0 ]
[ 105202-02-6 ]
[ 1160166-35-7 ]

Reference： [1]Applied Organometallic Chemistry,2016,vol. 30,p. 446 - 450

55
[ 16939-57-4 ]
[ 105202-02-6 ]
[ 75-36-5 ]
(S,E)-1-(2-styryl-6-(trifluoromethyl)indolin-1-yl)ethanone [ No CAS ]
(R,E)-1-(2-styryl-6-(trifluoromethyl)indolin-1-yl)ethanone [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 9402 - 9408

56
[ 105202-02-6 ]
2-iodo-3',5-bis(trifluoromethyl)-1,1'-biphenyl [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 5192 - 5195

57
[ 105202-02-6 ]
2,11-bis(trifluoromethyl)triphenylene [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 5192 - 5195

58
[ 105202-02-6 ]
[ 1423-26-3 ]
3',5-bis(trifluoromethyl)-[1,1'-biphenyl]-2-amine [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 5192 - 5195

59
[ 105202-02-6 ]
1-(2-iodo-5-(trifluoromethyl)phenyl)-1H-1,2,3-triazole [ No CAS ]

Reference： [1]Patent: WO2017/37682,2017,A1

60
[ 105202-02-6 ]
2-azido-1-iodo-4-(trifluoromethyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%		2-Iodo-5-(trifluoromethyl) aniline (13g, 45.3mmol) was dissolved in a mixture of water (100 ml) and acetonitrile (50 ml) into which HC1 (34.4 ml, 1132 mmol) was added. The solution was cooled to -5 C and a solution of sodium nitrite (4.69g, 67.9 mmol) in water was added slowly. The solution was stirred at that temperature for 30 mm after which asolution of sodium azide (4.42 g, 67.9 mmol) was added to this mixture. The solution was warmed to room temperature over another 30 mm and the reaction mixture was extracted with ethyl acetate and the ethyl acetate layer dried and concentrated to obtain the product as viscous dark oil (14 g, 99%). 1H NMR (400 MHz, Chloroform-d) 7.95 (d, J = 8.2 Hz, 1H), 7.35 (s, 1H), 7.14 (d, J= 8.2 Hz, 1H).

Reference： [1]Patent: WO2017/37682,2017,A1 .Location in patent: Page/Page column 61

61
[ 105202-02-6 ]
1-(2-iodo-5-(trifluoromethyl)phenyl)-4-(trimethylsilyl)-1H-1,2,3-triazole [ No CAS ]

Reference： [1]Patent: WO2017/37682,2017,A1

62
[ 105202-02-6 ]
[ 536-74-3 ]
[ 2258-42-6 ]
C₁₆H₁₀F₃NO [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 6905 - 6908

63
[ 119072-55-8 ]
[ 124-38-9 ]
[ 105202-02-6 ]
3-(tert-butyl)-7-(trifluoromethyl)quinazoline-2,4(1H,3H)-dione [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 4484 - 4487

64
[ 59648-31-6 ]
[ 105202-02-6 ]
10,11-dihydro-8-trifluoromethyl-11-oxodibenz[b,f][1,4]oxazepine-2-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With 1,1'-bis-(diphenylphosphino)ferrocene; copper(l) iodide; [ruthenium(II)(eta6-1-methyl-4-isopropyl-benzene)(chloride)(mu-chloride)]2; sodium hydroxide; In toluene; at 120℃; for 40h;	In a air atmosphere, 1.0 mmol of 5-carboxymethyl-2-hydroxybenzylalcohol , 1.2 mmol of <strong>[105202-02-6]5-trifluoromethyl-2-iodoaniline</strong>,0.02 mmol p-cymene ruthenium dichloride dimer,0.03 mmol of cuprous iodide, 0.08 mmol of 1,1'-bis (diphenylphosphino) ferrocene,5.0 mmol of sodium hydroxide, and 5 ml of toluene, and then placed on a condenser tube heated to 120 C. with an oil bath with magnetic stirring for 40 hours. The oil bath was removed, 3 ml of water was added to the reaction mixture and the mixture was extracted three times with 5 ml of ethyl acetate. The organic phases were combined and dried over anhydrous magnesium sulfate for 30 minutes. The filtrate was concentrated on a rotary evaporator. The concentrated solid was extracted with methylene chloride , Recrystallized to give pure product 23, yield 81%.

Reference： [1]Patent: CN105949143,2016,A .Location in patent: Paragraph 0024

65
[ 105202-02-6 ]
[ 192314-71-9 ]
C₂₃H₂₉F₃N₂O₆ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 6002 - 6017

66
[ 105202-02-6 ]
C₂₂H₂₇F₃N₂O₆ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 6002 - 6017

67
[ 105202-02-6 ]
C₃₆H₄₃ClF₃N₅O₅ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 6002 - 6017

68
[ 105202-02-6 ]
(S)-2-amino-N-(1-((5-chloro-1H-indol-3-yl)methyl)piperidin-4-yl)-3-(6-(trifluoromethyl)-1H-indol-3-yl)propanamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 6002 - 6017

69
[ 105202-02-6 ]
3-bromo-2-chloro-4-ethylbenzotrifluoride [ No CAS ]

Reference： [1]Patent: WO2006/118155,2006,A1

70
[ 105202-02-6 ]
N-methyl-3-(6'-ethyl-2'-chloro-3'-trifluoromethylphenyl)benzamide [ No CAS ]

Reference： [1]Patent: WO2006/118155,2006,A1

71
[ 105202-02-6 ]
3-(2'-chloro-6'-ethyl-3'-trifluoromethylphenyl)-benzoic acid ethyl ester [ No CAS ]

Reference： [1]Patent: WO2006/118155,2006,A1

72
[ 105202-02-6 ]
[ 914643-00-8 ]

Reference： [1]Patent: WO2006/118155,2006,A1

73
[ 627-19-0 ]
[ 105202-02-6 ]
C₁₂H₁₂F₃N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; In acetonitrile;Inert atmosphere; Reflux;	General procedure: PdCl2(PPh3)2 (35.1 mg, 0.05 mmol), CuI (9.5 mg, 0.05 mmol), PPh3 (13.1 mg, 0.05 mmol) and iodoaniline derivatives (1.00 mmol) were stirred under N2 in a mixed solvent with CH3CN (5 mL) and Et3N (1 mL). The alkyne (1.20 mmol) was added to the mixture and stirred in reflux. The reaction was monitored by TLC. After completion, H2O (10 mL) was added to the reaction mixture and extracted with ethyl acetate (3 × 10 mL). The combined organic solution was washed with brine, dried over anhydrous MgSO4, concentrated at the reduced pressure. And the crude product was purified by column chromatography to give 2-alkynylanilines.

Reference： [1]Tetrahedron Letters,2018,vol. 59,p. 3719 - 3723

74
[ 105202-02-6 ]
C₁₉H₁₈F₃NO₂S [ No CAS ]

Reference： [1]Tetrahedron Letters,2018,vol. 59,p. 3719 - 3723

75
[ 105202-02-6 ]
C₁₉H₁₈F₃NO₂S [ No CAS ]

Reference： [1]Tetrahedron Letters,2018,vol. 59,p. 3719 - 3723

76
[ 105202-02-6 ]
(E)-2-cyclopentyl-1-(methoxymethyl)-3-(3,3,3-trifluoro-1-(thiophen-2-yl)prop-1-en-1-yl)-6-(trifluoromethyl)-1H-indole [ No CAS ]