860457-99-4|Ethyl 6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate| Ambeed

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Quality Control of [ 860457-99-4 ] Purity: 95+% SDS Specification

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Product Details of [ 860457-99-4 ]

CAS No. :	860457-99-4
Formula :	C₁₁H₉F₃N₂O₂
M.W :	258.20
SMILES Code :	CCOC(=O)C1=CN2C=C(C=CC2=N1)C(F)(F)F
MDL No. :	MFCD11100212
InChI Key :	NPJTXOGHERSPFX-UHFFFAOYSA-N
Pubchem ID :	27282727

Safety of [ 860457-99-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 860457-99-4 ]

* 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.

Downstream synthetic route of [ 860457-99-4 ]

[ 860457-99-4 ] Synthesis Path-Downstream 1~33

1
[ 70-23-5 ]
[ 74784-70-6 ]
[ 860457-99-4 ]

Yield	Reaction Conditions	Operation in experiment
42%	In methanol; 1,2-dimethoxyethane; at 80℃; for 14.0h;	To a mixed solution of 5-(trifluoromethyl)pyridin-2-amine (835 mg, 5.15 mmol) in 1,2-dimethoxyethane (12.9 mL) and methanol (12.9 mL) was added ethyl bromopyruvate (776 μL, 6.18 mmol), and the mixture was stirred for 14 hours at 80C. After concentrating the reaction solution under reduced pressure, the residue was purified by silica gel column chromatography to give ethyl 6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate (amount 557 mg, yield 42%).
42%	In methanol; 1,2-dimethoxyethane; at 80℃; for 14.0h;	5- (Trifluoromethyl) Pyridine-2-amine (835 mg, 5.15 mmol)In a mixed solution of 1,2-dimethoxyethane (12.9 mL) and methanol (12.9 mL)Ethyl bromopyruvic acid (776 μL, 6.18 mmol) was added, and the mixture was stirred at 80 C. for 14 hours.Residue after concentrating the reaction under reduced pressureWas purified by silica gel column chromatography to obtain ethyl 6- (trifluoromethyl) imidazole [1,2-a]pyridine-2-carboxylate (yield 557 mg, yield 42%).
	In ethanol; at 20 - 80℃; for 66.0h;	(a) 6-Trifluoromethyl-imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester. A mixture of 3-bromo-2-oxo-propionic acid ethyl ester (6.4 mL, 50.9 mmol, Aldrich) and 5-trifluoromethyl-pyridin-2-ylamine (1.65 g, 10.2 mmol, Maybridge) in EtOH (20 mL) was heated at 80 C. for 48 h, and left at room temperature for 18 h. The white solid that precipitated was filtered, and the filter cake was rinsed with ether (10 mL), and dried in vacuo to provide the title compound. MS (ESI, pos. ion.) m/z: 258 (M+1).

	With Sodium hydrogenocarbonate; In ethanol; at 85℃; for 4.0h;	To a solution of 5-(trifluoromethyl)pyridin-2-amine (4.0 g, 25 mmol) in ethanol (40 mL) were added ethyl 3-bromo-2-oxo-propanoate (3.7 mL, 30 mmol) and sodium bicarbonate (4.1 g, 49 mmol) at room temperature. The reaction mass was heated at 85 C for 4 hours. After completion, the reaction mass 5 was added to ice cold water, solid was precipitated and the obtained solid was filtered through a Buchner funnel to afford ethyl 6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate. This material was used as such in the next step. LCMS (Method 2): Rt = 1.35 min, m/z= 259 (M+H)+.
	With Sodium hydrogenocarbonate; In ethanol; at 85℃; for 4.0h;	To a solution of 5-(trifluoromethyl)pyridin-2-amine (4.0 g, 25 mmol) in ethanol (40 mL) were added ethyl 3-bromo-2-oxo-propanoate (3.7 mL, 30 mmol) and sodium bicarbonate (4.1 g, 49 mmol) at room temperature. The reaction mass was heated at 85 C for 4 hours. After completion, the reaction mass 5 was added to ice cold water, solid was precipitated and the obtained solid was filtered through a Buchner funnel to afford ethyl 6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate. This material was used as such in the next step. LCMS (Method 2): Rt = 1.35 min, m/z= 259 (M+H)+.

References: [1]Patent: EP3851436,2021,A1 .Location in patent: Paragraph 0273-0274.
[2]Patent: JP2021/138690,2021,A .Location in patent: Paragraph 0331-0333.
[3]Patent: US2005/165049,2005,A1 .Location in patent: Page/Page column 23.
[4]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 359 - 362.
[5]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 1572 - 1575.
[6]Patent: WO2022/49144,2022,A1 .Location in patent: Page/Page column 87-89.
[7]Patent: WO2022/49144,2022,A1 .Location in patent: Page/Page column 87-89.

2
[ 860457-99-4 ]
C₁₈H₁₃BrF₃N₅O [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 359 - 362.

3
[ 860457-99-4 ]
C₂₈H₃₂F₃N₅O₂Si [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 359 - 362.

4
[ 860457-99-4 ]
C₂₂H₁₈F₃N₅O₂ [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 359 - 362.

5
[ 860457-99-4 ]
C₂₂H₂₂F₃N₅O₂ [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 359 - 362.

6
[ 860457-99-4 ]
C₉H₇F₃N₂O [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 359 - 362.

7
[ 860457-99-4 ]
C₉H₆BrF₃N₂O [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 359 - 362.

8
[ 860457-99-4 ]
C₉H₅BrClF₃N₂ [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 359 - 362.

9
[ 860457-99-4 ]
C₁₆H₁₁ClF₃N₃O₄S [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 1572 - 1575.

10
[ 860457-99-4 ]
C₉H₅F₃N₂O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 1572 - 1575.

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In 1,4-dioxane; at 100℃; for 12.0h;	General procedure: To a stirred solution of 5-bromopyridin-2-amine(A14, 10 g, 57.8 mmol) in l,4-dioxane(120 mL) was added ethyl 3-bromo pyruvate(A15, 10.83 mL, 86.71 mmol), followed by NaHC03(9.71 g, 115.6 mmol). The reaction mixture was heated for 12 h at 100 C and then concentrated under reduced pressure. The crude product was washed with ethyl acetate/water 2: 1 mixture(3x 75 mL) and the combined organic layer was concentrated. Purified by column chromatography using ethyl acetate/hexane to afford 16 as blackish brown solid(15.3 g, 98%). MS(ESI) m/z =271[M+H]+.

12
[ 860457-99-4 ]
ethyl 6-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 20% palladium hydroxide on carbon; hydrogen; acetic acid; In tetrahydrofuran; ethanol; at 20℃; under 2280.15 Torr; for 16.0h;	To a mixed solution of <strong>[860457-99-4]ethyl 6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate</strong> (5.96 g, 23.1 mmol) in tetrahydrofuran (100 mL), ethanol (100 mL) and acetic acid (11.9 mL) was added 20% palladium hydroxide on carbon (2.43 g). The mixture was stirred under pressurized conditions (about 3 atm) at hydrogen atmosphere for 16 hours at room temperature. The reaction solution was filtered through celite and the solvent was evaporated off under reduced pressure. To the residue was added toluene, and the solvent was evaporated off under reduced pressure to give ethyl 6-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxylate (amount 6.42 g) as a crude product.
	With 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid; In tetrahydrofuran; ethanol; at 20℃; under 2280.15 Torr; for 16.0h;	Ethyl 6- (trifluoromethyl) imidazole [1,2-a]pyridine-2-carboxylate (5.96)g, 23.1 mmol) tetrahydrofuranAdd 20% palladium hydroxide carbon (2.43 g) to a mixed solution of (100 mL), ethanol (100 mL) and acetic acid (11.9 mL), and under pressure (about 3 atm), hydrogen.The mixture was stirred at room temperature for 16 hours in an atmosphere.The reaction mixture was filtered through Celite, and then the solvent was distilled off under reduced pressure. Toluene was added to the residue, and the solvent was distilled off under reduced pressure.Ethyl 6- (trifluoromethyl)-5,6,7,8-tetrahydroimidazole [1,2-a]pyridine-2-carboxylate (yield 6.42 g) was obtained as a crude product.

References: [1]Patent: EP3851436,2021,A1 .Location in patent: Paragraph 0273; 0275.
[2]Patent: JP2021/138690,2021,A .Location in patent: Paragraph 0331-0332; 0334.

13
[ 860457-99-4 ]
6-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxylic acid [ No CAS ]

References: [1]Patent: EP3851436,2021,A1 .
[2]Patent: JP2021/138690,2021,A .

14
[ 860457-99-4 ]
N-(6-fluorochroman-3-yl)-6-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxamide [ No CAS ]

References: [1]Patent: EP3851436,2021,A1 .
[2]Patent: JP2021/138690,2021,A .

15
[ 860457-99-4 ]
(R)-N-(6-ethylchroman-3-yl)-2,2,2-trifluoroacetamide [ No CAS ]

References: [1]Patent: EP3851436,2021,A1 .Location in patent: Paragraph 0289; 0300.

16
[ 860457-99-4 ]
N-((R)-6-chlorochroman-3-yl)-6-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxamide hydrochloride [ No CAS ]

References: [1]Patent: EP3851436,2021,A1 .

17
[ 860457-99-4 ]
N-((R)-6-chlorochroman-3-yl)-N-methyl-6-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxamide [ No CAS ]

References: [1]Patent: EP3851436,2021,A1 .

18
[ 860457-99-4 ]
N-((R)-6-chlorochroman-3-yl)-6-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxamide [ No CAS ]

References: [1]Patent: EP3851436,2021,A1 .
[2]Patent: JP2021/138690,2021,A .

19
[ 860457-99-4 ]
C₁₈H₁₇ClF₃N₃O₂ [ No CAS ]
C₁₈H₁₇ClF₃N₃O₂ [ No CAS ]

References: [1]Patent: JP2021/138690,2021,A .

20
[ 860457-99-4 ]
[ 1135283-40-7 ]

Yield	Reaction Conditions	Operation in experiment
	With N-chloro-succinimide; In N,N-dimethyl-formamide; at 40℃; for 4.0h;	To a solution of <strong>[860457-99-4]ethyl 6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate</strong> (Intermediate I-4 prepared as described above) (8.5 g, 33 mmol) in N,N-dimethylformamide (85 mL) was added 1- chloropyrrolidine-2,5-dione (5.3 g, 40 mmol) at room temperature. The reaction mass was heated at 40 15 C for 4 hours. After completion, the reaction mass was quenched with ice cold water, solid was precipitated and the obtained solid was filtered through a Buchner funnel, dried in vacuo to afford ethyl 3-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate as a solid. LCMS (Method 2): Rt= 1.45 min, m/z=293 (M+H)+.
	With N-chloro-succinimide; In N,N-dimethyl-formamide; at 40℃; for 4.0h;	To a solution of <strong>[860457-99-4]ethyl 6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate</strong> (Intermediate I-4 prepared as described above) (8.5 g, 33 mmol) in N,N-dimethylformamide (85 mL) was added 1- chloropyrrolidine-2,5-dione (5.3 g, 40 mmol) at room temperature. The reaction mass was heated at 40 15 C for 4 hours. After completion, the reaction mass was quenched with ice cold water, solid was precipitated and the obtained solid was filtered through a Buchner funnel, dried in vacuo to afford ethyl 3-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate as a solid. LCMS (Method 2): Rt= 1.45 min, m/z=293 (M+H)+.

References: [1]Patent: WO2022/49144,2022,A1 .Location in patent: Page/Page column 87; 89.
[2]Patent: WO2022/49144,2022,A1 .Location in patent: Page/Page column 87; 89.

21
[ 860457-99-4 ]
ethyl 3-ethylsulfanyl-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate [ No CAS ]

References: [1]Patent: WO2022/49144,2022,A1 .

22
[ 860457-99-4 ]
ethyl 3-ethylsulfonyl-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylate [ No CAS ]

References: [1]Patent: WO2022/49144,2022,A1 .

23
[ 860457-99-4 ]
3-ethylsulfonyl-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid [ No CAS ]

References: [1]Patent: WO2022/49144,2022,A1 .

24
[ 860457-99-4 ]
tert-butyl N-[3-ethylsulfonyl-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]carbamate [ No CAS ]