438554-45-1|4-Chloro-5-nitro-2-(trifluoromethyl)pyridine| Ambeed

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Quality Control of [ 438554-45-1 ] Purity: 95% SDS Specification

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Product Details of [ 438554-45-1 ]

CAS No. :	438554-45-1
Formula :	C₆H₂ClF₃N₂O₂
M.W :	226.54
SMILES Code :	[O-][N+](=O)C1=CN=C(C=C1Cl)C(F)(F)F
MDL No. :	MFCD11848352
InChI Key :	VBVLYVRVIUJULO-UHFFFAOYSA-N
Pubchem ID :	22380051

Safety of [ 438554-45-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 438554-45-1 ]

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

Downstream synthetic route of [ 438554-45-1 ]

[ 438554-45-1 ] Synthesis Path-Downstream 1~19

1
[ 438554-44-0 ]
[ 438554-45-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	With phosphorus pentachloride; trichlorophosphate; at 80℃; for 16.0h;	To a stirred solution of 5-nitro-2-(trifluoromethyl)pyridin-4-ol (3.9g, 0.Ol4mol), PCI5 (4.5g, 0.O2lmol) and POOl3 (2 mL, 0.O2mol) was heated to 80 00 for 16h. The TLC showed reaction to be complete. The reaction mixture was cooled to room temperature, diluted with DCM and washed with water (lOOmL), saturated NaHCO3 solution (lOOmL) and brine (lOOmL). The organics were dried (Na2SO4), filtered andconcentrated under reduced pressure to afford 4-chloro-5-nitro-2-(trifluoromethyl)pyridine as yellow oil. Yield: 3g (94%); 1H NMR (400 MHz; DMSOd 6): 9.42 (5, 1H), 8.56 (5, 1H); MS (ESl+) for CHNOS m/z227.34 [M+H].
83%	With phosphorus pentachloride; trichlorophosphate; at 80℃; for 11.0h;	A mixture of compound 6.1 (570 mg, 2.74 mmol), phosphorus pentachloride (900 mg, 4.11 mmol, 1.5 equiv), and phosphorus oxychloride (0.38 mL, 4.11 mmol, 1.5 equiv) was heated to 80 C and stirred 11 hours. After cooling to room temperature, the reaction mixture was transferred to ice cold water and the mixture was extracted with dichloromethane (4 X 40 mL). The combined organic layers were washed with sat'd aqueous NaHCO3 (50 mL), water (50 mL), and brine (50 mL), dried over anhydrous sodium sulfate, and concentrated. Compound 6.2 (512 mg, 83%) was isolated as a yellow oil that was used without further purification.
	With phosphorus pentachloride; trichlorophosphate;	2. Preparation of 4-Chloro-5-nitro-2-trifluoromethyl-pyridine The crude 5-nitro-2-trifluoromethyl-pyridin-4-ol (3.4 g, 16.3 mmmol) was treated with PCl5 (5.2 g, 24.97 mmol) and POCl3 (7 mL, 24.49 mmol). The resulting mixture is heated at 80 C. for 18 h, cooled and poured into ice-cold water, and extracted with CH2Cl2. The combined organic phase is washed successively with saturated aqueous NaHCO3, water, brine, dried over Na2SO4, and concentrated in vacuo to afford 4-Chloro-5-nitro-2-trifluoromethyl-pyridine as an yellow oil. 1H NMR (300 MHz, CDCl3): delta 9.17 (s, 1H), 7.9 (s, 1H)

References: [1]Patent: WO2018/37223,2018,A1 .Location in patent: Page/Page column 107; 193; 194.
[2]Patent: WO2006/65703,2006,A1 .Location in patent: Page/Page column 108.
[3]Patent: US2003/69257,2003,A1 .

2
[ 438554-45-1 ]
[ 438564-36-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With ammonia; In ethanol; at 20℃; for 1.5h;	A pressure vessel was charged with compound 6.1 (512 mg, 0.51 mmol) and a saturated solution of ammonia in ethanol (15 mL). The vessel was sealed and the reaction mixture was stirred at room temperature for 1.5 hours, whereupon the reaction mixture was concentrated. Compound 6.3 (538 mg, >100%) was isolated as an orange solid, contaminated with inorganic salts.
96%	In tetrahydrofuran;	1. Preparation of 5-Nitro-2-trifluoromethyl-pyridin-4-ylamine Ammonia gas is bubbled through a solution of 2-trifluoromethyl-4-chloro-5-nitro-pyridine (4.12 g,18.23 mmol) in anhydrous THF at room temperature for 3 h. Removal of solvent under reduced pressure affords 5-nitro-2-trifluoromethyl-pyridin-4-ylamine (3.6 g, 96%); 1H NMR (300 MHz, CDCl3): delta 7.15 (s, 1H), 9.15 (s,1H).

References: [1]Patent: WO2006/65703,2006,A1 .Location in patent: Page/Page column 109.
[2]Patent: US2003/69257,2003,A1 .

3
EtNH₂ [ No CAS ]
[ 438554-45-1 ]
[ 438554-46-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In tetrahydrofuran; acetonitrile;	3. Preparation of Ethyl-(5-nitro-2-trifluoromethyl-pyridin-4-yl)-amine K2CO3 (4.15 g, 30.01 mmol), and 2.0 M solution of EtNH2 (15 mL, 30.01 mmol) in THF are added to a solution of <strong>[438554-45-1]4-chloro-5-nitro-2-trifluoromethyl-pyridine</strong> (3.4 g, 15.0 mmol) in acetonitrile (30 mL) under cold conditions. The reaction is complete after stirring at 0 C. for 2 h. Usual work up affords ethyl-(5-nitro-2-trifluoromethyl-pyridin-4-yl)-amine as an yellow-orange viscous oil. 1H NMR (300 MHz, CDCl3): delta 9.24 (s, 1H), 7.09 (s, 1H), 3.45 (t, J=7.2 Hz, 2H), 1.42 (t, J=7.2 Hz, 3H).

References: [1]Patent: US2003/69257,2003,A1 .

4
[ 438554-45-1 ]
[ 1437789-75-7 ]
[ 1456507-30-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 80℃; for 2.0h;	To a vial charged with (S)-3-((lr,4S)-4-aminocyclohexyl)-5,5- dimethyl-4-phenyloxazolidin-2-one (0.094 g, 0.326 mmol) were added ACN (1.087 mL), DIEA (0.1 14 mL, 0.652 mmol) and <strong>[438554-45-1]4-chloro-5-nitro-2-(trifluoromethyl)pyridine</strong> (commercially available from Abby Pharmatech, LLC, Newark, NJ) (0.078 g, 0.342 mmol) respectively. The vial was sealed and heated at 80C for 2 hours providing a brown solution with product as the main species according to LC-MS. The solution was dried under reduced pressure and purified with a 25 g SNAP column (Biotage) ramping DCM:MeOH (90: 10) in DCM (0 - 25%, then isocratic at 25%, 215 nm detection) providing (S)-5,5-dimethyl-3-((lr,4S)-4-((5-nitro-2-(trifluoromethyl)pyridin- 4-yl)amino)cyclohexyl)-4-phenyloxazolidin-2-one (0.150 g, 0.314 mmol, 96 % yield) as a yellow solid, m/z (ESI) 479.0 (M+H)+.

References: [1]Patent: WO2013/134079,2013,A1 .Location in patent: Paragraph 0494-0495.

5
[ 438554-45-1 ]
[ 1456507-31-5 ]

References: [1]Patent: WO2013/134079,2013,A1 .

6
[ 438554-45-1 ]
[ 1456505-17-1 ]

References: [1]Patent: WO2013/134079,2013,A1 .

7
[ 438554-45-1 ]
N-(6-(trifluoromethyl)-1H-imidazo[4,5-c]pyridin-2-yl)benzo[d]oxazol-2-amine [ No CAS ]

References: [1]Patent: WO2018/37223,2018,A1 .

8
[ 438554-45-1 ]
[ 438564-37-5 ]

References: [1]Patent: WO2018/37223,2018,A1 .

9
[ 438554-45-1 ]
; 194 [ No CAS ]
[ 438564-36-4 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; In ethanol; at -78 - 20℃; for 2.25h;Sealed tube;	To a stirred solution of <strong>[438554-45-1]4-chloro-5-nitro-2-(trifluoromethyl)pyridine</strong> (ig, 4.42mmol) in ethanol (7mL) in sealed tube, NH3 gas was purged at -78 00 for 15 mm. The reaction mixture was stirred at room temperature for 2h. The TLC showed reaction to be complete. The reaction mixture was evaporated under reduced pressure to afford 5-nitro-2-(trifluoromethyl)pyridin-4-amine as yellow solid. Yield: ig (crude); 1H NMR (400 MHz; DMSO-d6): 9.02 (5, 1H), 7.39 (5, 1H); MS (ESl+) for CHNOS m/z 208.20 [M+H].

References: [1]Patent: WO2018/37223,2018,A1 .Location in patent: Page/Page column 107; 193; 194.

10
[ 170886-13-2 ]
[ 438554-45-1 ]

References: [1]Patent: WO2018/37223,2018,A1 .
[2]Patent: US2003/69257,2003,A1 .

11
[ 438554-45-1 ]
[ 438564-35-3 ]

References: [1]Patent: US2003/69257,2003,A1 .

12
[ 438554-45-1 ]
[ 438554-47-3 ]

References: [1]Patent: US2003/69257,2003,A1 .

13
[ 438554-45-1 ]
[ 438553-88-9 ]

References: [1]Patent: US2003/69257,2003,A1 .

14
[ 438554-45-1 ]
[ 126726-62-3 ]
5-nitro-4-(prop-1-en-2-yl)-2-(trifluoromethyl)pyridine [ No CAS ]