261952-16-3|1-(Bromomethyl)-2-methyl-3-(trifluoromethyl)benzene| Ambeed

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Quality Control of [ 261952-16-3 ] Purity: 98% SDS Specification

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Product Details of [ 261952-16-3 ]

CAS No. :	261952-16-3
Formula :	C₉H₈BrF₃
M.W :	253.06
SMILES Code :	FC(C1=C(C)C(CBr)=CC=C1)(F)F
MDL No. :	MFCD01631608
InChI Key :	YSABBOPLIUMXKY-UHFFFAOYSA-N
Pubchem ID :	2775617

Safety of [ 261952-16-3 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H314
Precautionary Statements:	P280-P305+P351+P338-P310
Class:	8
UN#:	1760
Packing Group:	Ⅲ

Application In Synthesis of [ 261952-16-3 ]

* 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 [ 261952-16-3 ]

[ 261952-16-3 ] Synthesis Path-Downstream 1~35

1
[ 261952-16-3 ]
[ 1256290-35-3 ]
[ 1256290-36-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 3h;	To a 1 L round bottom flask containing a stirred suspension of N-[5-cyano-2-(4- morpholinyl)-l,3-thiazol-4-yl]acetamide (20.Og, 79 mmol) and K2CO3 (23.01 g, 166 mmol) in N,N-Dimethylformamide (DMF) (25OmL) was added l-(bromomethyl)-2- methyl-3-(trifluoromethyl)benzene (20.06 g, 79 mmol). The reaction was heated to 90 0C and was maintained at 90 0C for 3hr. LC/MS at this point indicated predominantly product, so the reaction was cooled to room temperature, partitioned between water (500 mL) and ethyl acetate (500 mL). The layers were separated, and then the aqueous layer was extracted with ethyl acetate (3 x 100 rnL). The combined organic layers were dried over sodium sulfate, then concentrated to leave N-[5-cyano-2-(4-morpholinyl)-l,3-thiazol-4- yl]-N-[2-methyl-3-(trifluoromethyl)phenyl]methyl}acetamide (27.1 g, 63.8 mmol, 81 % yield) as a residual oil that was carried onto the next step without further purification. IH NMR (400 MHz, DMSO-J6) δ ppm 2.11 (s, 3 H) 2.36 (s, 3 H) 3.43 - 3.52 (m, 4 H) 3.64 - 3.74 (m, 4 H) 4.99 (s, 2 H) 7.33 (t, J=7.83 Hz, 1 H) 7.43 (d, J=7.58 Hz, 1 H) 7.60 (d, J=7.83 Hz, 1 H)

References: [1]Patent: WO2010/135504,2010,A1 .Location in patent: Page/Page column 62-63.
[2]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 524 - 529.

2
[ 261952-16-3 ]
[ 1366126-64-8 ]
[ 1366126-83-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2230 - 2234.

3
[ 261952-16-3 ]
[ 1366126-65-9 ]
[ 1366126-84-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2230 - 2234.

4
[ 261952-16-3 ]
[ 1366126-67-1 ]
[ 1366126-87-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2230 - 2234.

5
[ 261952-16-3 ]
[ 57473-33-3 ]
[ 1366126-81-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2230 - 2234.

6
[ 261952-16-3 ]
[ 1372540-59-4 ]
[ 1372540-63-0 ]

Yield	Reaction Conditions	Operation in experiment
70%		A suspension of 4-bromo-2-methyl-6-(4-morpholinyl)-1H-benzimidazole, prepared as described in Example 62 (500 mg, 1.688 mmol) and potassium carbonate (700 mg, 5.06 mmol) in N,N-Dimethylformamide (DMF) (6 mL) was stirred at rt for 15 min. <strong>[261952-16-3]1-(bromomethyl)-2-methyl-3-(trifluoromethyl)benzene</strong> (641 mg, 2.53 mmol) was added in and the resulting reaction mixture was stirred for 3 h at 80 C. It was then cooled to room temperature and poured into ice/water. The precipitate was collected by filtration, washed with water, then few mLs of hexanes and air dried. The crude material was purified on a silica gel column (ISCO, 0-80% EtOAc in hexanes) to the desired product (565 mg, 1.182 mmol, 70.0% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.59 (d, J=7.83 Hz, 1H), 7.16 (d, J=2.02 Hz, 1H), 7.10-7.15 (m, 1H), 6.46-6.52 (m, 2H), 5.25 (s, 2H), 3.75-3.89 (m, 4H), 3.05-3.14 (m, 4H), 2.55 (s, 3H), 2.51 (s, 3H). MS(ES+) m/e 468.9 [M+H]+.

References: [1]Patent: US2012/88767,2012,A1 .Location in patent: Page/Page column 48.

7
[ 261952-16-3 ]
[ 1372540-21-0 ]
[ 1372540-24-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 3h;	A solution of methyl 2-methyl-5-(4-morpholinyl)-1H-benzimidazole-7-carboxylate prepared as described in Example 26, step d (500 mg, 1.8 mmol), <strong>[261952-16-3]1-(bromomethyl)-2-methyl-3-(trifluoromethyl)benzene</strong> (483 mg, 1.9 mmol) and K2CO3 (497 mg, 3.6 mmol) in DMF (50 mL) was stirred at 80 C. for 3 h. The reaction mixture was cooled to rt and poured into water (50 mL), extracted with EtOAc (30 mL*3). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel chromatography eluted with DCM:MeOH=50:1 to give the crude product (230 mg, yield 29%), as a white solid. 1H NMR (300 MHz, DMSO-d6): δ ppm 2.39 (s, 3H), 2.54 (s, 3H), 3.08 (t, 4H, J=4.8 Hz), 3.72 (t, 4H, J=4.8 Hz), 3.89 (s, 3H), 5.57 (s, 2H), 6.27 (d, 1H, J=7.5 Hz), 7.22 (t, 1H, J=7.5 Hz), 7.27 (d, 1H, J=2.4 Hz), 7.38 (d, 1H, J=2.4 Hz) 7.60 (d, 1H, J=7.5 Hz); LC-MS: m/e=448 [M+1]+

References: [1]Patent: US2012/88767,2012,A1 .Location in patent: Page/Page column 35.

8
[ 261952-16-3 ]
[ 1372540-68-5 ]
[ 1372540-72-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 18h;	A mixture of methyl 2-(difluoromethyl)-5-(4-morpholinyl)-1H-benzimidazole-7-carboxylate, prepared as described in Example 68 (500 mg, 1.6 mmol), K2CO3 (442 mg, 3.2 mmol) and <strong>[261952-16-3]1-(bromomethyl)-2-methyl-3-(trifluoromethyl)benzene</strong> (480 mg, 1.9 mmol) in DMF (15 mL) was stirred at 70 C. for 18 h. The reaction mixture was cooled to room temperature and filtered. The filtrate was poured into water (100 mL) and filtered, the filter cake was collected and purified by silica gel chromatography eluted with petroleum ether:EtOAc=1:1 to give the desired product (710 mg, 98%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6): δ ppm 2.53 (s, 3H), 3.14 (t, 4H, J=4.5 Hz), 3.73 (t, 4H, J=4.5 Hz), 3.93 (s, 3H), 5.75 (s, 2H), 6.27 (d, 1H, J=7.8 Hz), 7.22 (t, 1H, J=7.8 Hz), 7.30 (d, 1H, J=2.1 Hz), 7.36 (t, 1H, J=51.6 Hz), 7.58-7.61 (m, 2H); LC-MS: m/e=484 [M+1]+

References: [1]Patent: US2012/88767,2012,A1 .Location in patent: Page/Page column 51.

9
[ 261952-16-3 ]
[ 1372540-42-5 ]
[ 1372540-43-6 ]

Yield	Reaction Conditions	Operation in experiment
24.1%		A suspension of methyl 5-(4-morpholinyl)-2-(trifluoromethyl)-1H-benzimidazole-7-carboxylate, prepared as described in Example 45 (1.5 g, 4.56 mmol) and potassium carbonate (1.889 g, 13.67 mmol) in N,N-Dimethylformamide (DMF) (10 mL) was stirred at rt for 15 min. 1-(Bromomethyl)-2-methyl-3-(trifluoromethyl)benzene (1.729 g, 6.83 mmol) was added in and the resulting reaction mixture was stirred for 3 h at 80 C. The mixture was then cooled to room temperature and poured into ice/water. The precipitate was collected by filtration, washed with water, then hexanes (turned into a gum on the filter paper-some material was lost). The crude material was purified on a silica gel column (ISCO, eluting with 0-5% MeOH in DCM) to give the desired product (580 mg, 1.099 mmol, 24.12% yield) (several mixed fractions obtained were discarded). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.65 (d, J=2.53 Hz, 1H), 7.61 (d, J=7.83 Hz, 1H), 7.37 (d, J=2.27 Hz, 1H), 7.23 (t, J=7.96 Hz, 1H), 6.29 (d, J=7.58 Hz, 1H), 5.76 (s, 2H), 3.93 (s, 3H), 3.70-3.78 (m, 4H), 3.12-3.22 (m, 4H), 2.53 (s, 3H). MS(ES+) m/e 502 [M+H]+.

References: [1]Patent: US2012/88767,2012,A1 .Location in patent: Page/Page column 41.

10
[ 261952-16-3 ]
[ 1372540-65-2 ]
[ 1372540-66-3 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 1h;	To the mixture of methyl 2-chloro-5-(4-morpholinyl)-1H-benzimidazole-7-carboxylate, prepared as described in Example 65 (0.5 g, 1.691 mmol) in N,N-Dimethylformamide (DMF) (10 ml) was added in potassium carbonate (0.467 g, 3.38 mmol) and <strong>[261952-16-3]1-(bromomethyl)-2-methyl-3-(trifluoromethyl)benzene</strong> (0.428 g, 1.691 mmol). The reaction mixture was stirred at 80 C. for 1 h. The reaction was cooled down. Water (100 mL) was added in. The solid precipitated. Filtration gave the solid which was purified on a silica column (20~60% EtOAc/Hexane) to give the product as white solid (0.66 g, 83%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.54 (s, 3H) 3.07-3.16 (m, 4H) 3.68-3.78 (m, 4H) 3.91 (s, 3H) 5.63 (s, 2H) 6.41 (d, J=7.83 Hz, 1H) 7.28 (t, J=7.83 Hz, 1H) 7.39 (d, J=2.27 Hz, 1H) 7.50 (d, J=2.53 Hz, 1H) 7.63 (d, 1H). MS(ES+) m/e 468.0 [M+H]+.

References: [1]Patent: US2012/88767,2012,A1 .Location in patent: Page/Page column 49.

11
[ 261952-16-3 ]
[ 1374306-17-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3198 - 3202.

12
[ 261952-16-3 ]
[ 1374306-22-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3198 - 3202.

13
[ 261952-16-3 ]
[ 1374306-16-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3198 - 3202.

14
[ 261952-16-3 ]
[ 1374306-28-1 ]
[ 1374306-34-9 ]

Yield	Reaction Conditions	Operation in experiment
45%	With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 0.166667h;Microwave irradiation;	General procedure: A mixture of 5-chloro-2-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-ol (125 mg, 0.677 mmol), <strong>[261952-16-3]1-(bromomethyl)-2-methyl-3-(trifluoromethyl)benzene</strong> (189 mg, 0.745 mmol), K2CO3 (112 mg, 0.813 mmol) and N,N-Dimethylformamide (DMF) (3 mL) was irradiated in a Biotage Initiator microwave at 120 C for 10 min. Solution was diluted with EtOAc, washed with water, brine, dried (MgSO4), and concentrated. The crude material was purified on a Teledyne-Isco RediSep Rf silica gel column (4g) and was eluted with a gradient of ethyl acetate and hexanes (10-100%) over 10 minutes. The appropriate fractions were collected and evaporated to yield the expected compound (108mg, 45%). 1H NMR (400 MHz, CHLOROFORM-d) ppm 2.40 (s, 3H) 2.51 (s, 3H), 5.35 (s, 2 H) 6.30 (s, 1 H) 6.89 (d, 1H) 7.31 (t, 1 H) 7.68 (d, 1H) 8.02 (s, 1H); LC/MS: MS(ES+) m/e 367 (MH+).

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3198 - 3202.

15
[ 261952-16-3 ]
[ 1374306-29-2 ]
[ 1374306-35-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 0.166667h;Microwave irradiation;	General procedure: A mixture of 5-chloro-2-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-ol (125 mg, 0.677 mmol), <strong>[261952-16-3]1-(bromomethyl)-2-methyl-3-(trifluoromethyl)benzene</strong> (189 mg, 0.745 mmol), K2CO3 (112 mg, 0.813 mmol) and N,N-Dimethylformamide (DMF) (3 mL) was irradiated in a Biotage Initiator microwave at 120 C for 10 min. Solution was diluted with EtOAc, washed with water, brine, dried (MgSO4), and concentrated. The crude material was purified on a Teledyne-Isco RediSep Rf silica gel column (4g) and was eluted with a gradient of ethyl acetate and hexanes (10-100%) over 10 minutes. The appropriate fractions were collected and evaporated to yield the expected compound (108mg, 45%).

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3198 - 3202.

16
[ 261952-16-3 ]
[ 1374306-30-5 ]
[ 1374306-36-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 0.166667h;Microwave irradiation;	General procedure: A mixture of 5-chloro-2-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-ol (125 mg, 0.677 mmol), <strong>[261952-16-3]1-(bromomethyl)-2-methyl-3-(trifluoromethyl)benzene</strong> (189 mg, 0.745 mmol), K2CO3 (112 mg, 0.813 mmol) and N,N-Dimethylformamide (DMF) (3 mL) was irradiated in a Biotage Initiator microwave at 120 C for 10 min. Solution was diluted with EtOAc, washed with water, brine, dried (MgSO4), and concentrated. The crude material was purified on a Teledyne-Isco RediSep Rf silica gel column (4g) and was eluted with a gradient of ethyl acetate and hexanes (10-100%) over 10 minutes. The appropriate fractions were collected and evaporated to yield the expected compound (108mg, 45%).

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3198 - 3202.

17
[ 261952-16-3 ]
[ 1374306-38-3 ]
C₁₅H₁₂ClF₃N₄O [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3198 - 3202.

18
[ 261952-16-3 ]
[ 99967-88-1 ]
[ 1256289-45-8 ]

References: [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 524 - 529.

19
[ 261952-16-3 ]
[ 1256290-35-3 ]
[ 1256289-67-4 ]

References: [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 524 - 529.

20
[ 261952-16-3 ]
[ 70807-22-6 ]
[ 1420468-30-9 ]

Yield	Reaction Conditions	Operation in experiment
74%	In N,N-dimethyl-formamide; at 0 - 40℃; for 2.5h;Inert atmosphere;	To a solution of (1 -cyano-2-oxopropyl)sodium (3.5 g, 33.2 mmol) in N,N- Dimethylformamide (25 mL) stirred under nitrogen at 0C was added a solution of 1 - (bromomethyl)-2-methyl-3-(trifluoromethyl)benzene (7.0 g, 27.7 mmol) in 10 ml of DMF dropwise during 30 min. The reaction mixture was stirred at 40 C for 2 hours. Then this solution was diluted with saturated ammonium chloride solution. This solution was extracted with ethyl acetate (100 mL X 3). The combined organic layers were washed with water (30 mL) and brine (30 mL), dried, concentrated to dryness in vacuo. The crude product was purified with on a silica gel column to give 2-[2-methyl-3- (trifluoromethyl)phenyl]methyl}-3-oxobutanenitrile. (5.2 g, 74%). To a solution of 2-[2- methyl-3-(trifluoromethyl)phenyl]methyl}-3-oxobutanenitrile (5.2 g, 20.4 mmol) in ethanol (400 mL) stirred under nitrogen at 20C was added neat hydrazine monohydrate (2.25 g, 30.6 mmol) dropwise during 5 minutes. The reaction mixture was stirred at 100 C for overnight. After cooled to room temperature, the reaction mixture was evaporated to dryness in vacuo. The residue was purified on a silica gel column (methanol/DCM gradient solvent system) to provide titled product. (2.16 g, 39%); 1 H NMR (400 MHz, DMSO-c/6) δ ppm 1 .86 (s, 3 H) 2.39 (s, 3 H) 3.63 (s, 2 H) 4.30 (br. s., 2 H) 7.19 (d, J=7.58 Hz, 1 H) 7.27 (t, J=7.71 Hz, 1 H) 7.49 (s, 1 H) 1 1 .09 (br. s., 1 H)

References: [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 230 - 234.
[2]Patent: WO2013/28263,2013,A1 .Location in patent: Page/Page column 32; 33.

21
[ 261952-16-3 ]
[ 1420468-50-3 ]

References: [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 230 - 234.
[2]Patent: US9096605,2015,B2 .

22
[ 261952-16-3 ]
[ 1420468-55-8 ]

References: [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 230 - 234.
[2]Patent: US9096605,2015,B2 .

23
[ 261952-16-3 ]
[ 1420468-80-9 ]