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Quality Control of [ 957066-13-6 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 957066-13-6 ]

CAS No. :	957066-13-6	MDL No. :	MFCD09475917
Formula :	C₁₄H₁₇BBrF₃O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	380.99	Pubchem ID :	-
Synonyms :

Safety of [ 957066-13-6 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P201-P202-P261-P264-P270-P271-P280-P302+P352-P304+P340-P308+P313-P310-P330-P361-P403+P233-P405-P501	UN#:	1760
Hazard Statements:	H302-H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 957066-13-6 ]

* 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.

Downstream synthetic route of [ 957066-13-6 ]

[ 957066-13-6 ] Synthesis Path-Downstream 1~5

1
[ 957066-13-6 ]
[ 1030832-19-9 ]
[ 1030832-56-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h;	10.1 9- [N- [3- (methacrylamido) propylamino] methyl] -10- [N- [2- (tert-butoxycarbonyl) ethylamino] methyl] -anthracene (1, 0.2 g, 0.41 mmol) was placed into 150 mL round-bottom flask. It was dissolved in 5 mL of degassed dimethylformamide . 2- (Bromomethyl) -4-(trifluoromethoxy) phenylboronic acid pinacol ester (2g, 0.37, 0.97 mmol, 2.4 equiv.) was dissolved in 4 mL of N2 sparged DMF and added to reaction flask. The solution was stirred and flushed with N2 for 5 minutes. DIEA (0.6 mL, 3.5 mmol, 8.0 equiv.) was added to the reaction mixture and the solution was allowed to stir under a gentle stream of nitrogen and in the dark at ambient temperature overnight. After 24h the solvent was evaporated in vacuo. The residual product was dissolved in 10 mL of dichloromethane and extracted with 3 x 15 mL portions of phosphate buffer (0.1 M, pH 7.0). The dichloromethane solution was dried and evaporated in vacuo resulting in a golden oily residue. The crude product was stirred for 15 minutes with 5 mL of ether and then the solvent was removed. The yellow oily residue was kept under vacuum for 30 min resulting in foamy powder (3g, 0.41g, 91% yield) .RP-HPLC Conditions: HP 1100 HPLC chromatograph, Waters 3.9 x 150 mm NovaPak HR C18 column with guard column, 0.010 mL injection, 0.75 mL/min, 1.500 mL injection loop, 254 nm detection, A = water (0.1% v/v TFA) and B = MeCN (0.1% v/v TFA), gradient 10% B 2 min, 10-80% B over 18 min, 80-100% B over 2 min, 100 %B 2 min, retention time 15.0 min.

Reference： [1]Current Patent Assignee: SENSEONICS INC - WO2008/66921, 2008, A2 Location in patent: Page/Page column 40-41

2
[ 957066-13-6 ]
N-(4-fluoro-phenyl)-6-mercapto-nicotinamide [ No CAS ]
[ 1240494-30-7 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.5h;	3 Synthesis Example 3; Synthesis of Compound 19; As described in Method B, N-(4-fluoro-phenyl)-6-mercapto-nicotinamide IIa (372 mg, 1.5 mmol) and 2-bromomethyl-5-trifluoromethoxy-phenylboronic acid (572 mg, 1.5 mmol) were suspended in DMF (15 ml). To the reaction flask DIPEA (261 μL, 1.5 mmol) was added and the reaction was stirred for 30 minutes. Reaction completion was monitored by LC-MS. Cold water (100 mL) was added and the precipitate was collected by filtration and washed several times with cold water to afford 724.8 mg (88% yield, >90% purity by LC-MS) of the off-white solid product, 6-(2-boronic pinacol ester-5-trifluoromethoxy-benzylsulfanyl)-N-(4-fluoro-phenyl)-nicotinamide. ESI-MS m/z=549.1 [M+H+].
	With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.5h;	3 Synthesis Example 3 Synthesis of Compound 19 General procedure: As described in Method B, N-(4-fluoro-phenyl)-6-mercapto-nicotinamide IIa (372 mg, 1.5 mmol) and 2-bromomethyl-5-trifluoromethoxy-phenylboronic acid (572 mg, 1.5 mmol) were suspended in DMF (15 ml). To the reactionflask DIPEA (261 mL, 1.5 mmol) was added and the reaction was stirred for 30 minutes. Reaction completion wasmonitored by LC-MS. Cold water (100 mL) was added and the precipitate was collected by filtration and washed severaltimes with cold water to afford 724.8 mg (88% yield, >90% purity by LC-MS) of the off-white solid product, 6-(2-boronicpinacol ester-5-trifluromethoxy-benzylsulfanyl)-N-(4-fluoro-phenyl)-nicotinamide. ESI-MS m/z = 549.1 [M+H]+.

Reference： [1]Current Patent Assignee: SYNTRIX BIOSYSTEMS - US2010/210593, 2010, A1 Location in patent: Page/Page column 44
[2]Current Patent Assignee: SYNTRIX BIOSYSTEMS - EP2942346, 2015, A1 Location in patent: Paragraph 0091; 0146; 0147

3
[ 1240496-04-1 ]
[ 957066-13-6 ]
N-(4-fluorophenyl)-2-([2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethoxy)phenyl]methyl}sulfanyl)pyrimidine-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In N,N-dimethyl-formamide at 20℃; for 3.75h; Inert atmosphere;	3 Synthesis Example 3 Synthesis of Pinacol Ester Derivative 5 Synthesis Example 3 Synthesis of Pinacol Ester Derivative 5 [0136] [0137] 2-Mercapto-pyrimidine-5-carboxylic acid (4-fluoro-phenyl)-amide intermediate 4 (2.32 g, 9.3 mmol) and 2-bromomethyl-4-trifluoromethoxy-phenylboronic acid, pinacol ester (3.85 g, 10.1 mmol) were suspended in anhydrous DMF (20 ml). Sonication was used to dissolve the compounds. To the reaction flask triethylamine (2.8 mL, 20.1 mmol) was added and a precipitate (triethylamine-HBr) formed immediately. The reaction was layered with nitrogen gas and left to stand at room temperature for 3.75 hr. The reaction was poured into water (500 mL) and layered with ethyl acetate. The biphasic solution was transferred to a separatory funnel and diluted further with ethyl acetate and brine. The layers were separated, and the aqueous layer was extracted twice more with ethyl acetate. The combined ethyl acetate layers were dried over sodium sulfate, gravity filtered, and dried in vacu to yield 5.7 g (>100%, 93% pure by LC-MS) of a red oil, 2-[2-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)-5-trifluoromethoxy-benzylsulfanyl]-pyrimidine-5-carboxylic acid (4-fluoro-phenyl)-amide 6. ESI-MS m/z=550.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ 10.52 (s, 1H), 9.11 (s, 2H), 7.81 (d, J=8.2 Hz, 1H), 7.78-7.75 (m, 2H), 7.55 (s, 1H), 7.28-7.22 (m, 3H), 4.72 (s, 2H), 1.32 (s, 12H). The NMR spectrum also contained peaks consistent with the presence of residual DMF. The product was carried forward without further purification.
	With triethylamine In N,N-dimethyl-formamide at 20℃; for 3.75h; Inert atmosphere;	3 Synthesis of Pinacol Ester Derivative 5 2-Mercapto-pyrimidine-5-carboxylic acid (4-fluoro-phenyl)-amide intermediate 4 (2.32 g, 9.3 mmol) and 2-bromomethyl-4-trifluoromethoxy-phenylboronic acid, pinacol ester (3.85 g, 10.1 mmol) were suspended in anhydrous DMF (20 ml). Sonication was used to dissolve the compounds. To the reaction flask triethylamine (2.8 mL, 20.1 mmol) was added and a precipitate (triethylamine -HBr) formed immediately. The reaction was layered with nitrogen gas and left to stand at room temperature for 3.75 hr. The reaction was poured into water (500 mL) and layered with ethyl acetate. The biphasic solution was transferred to a separatory funnel and diluted further with ethyl acetate and brine. The layers were separated, and the aqueous layer was extracted twice more with ethyl acetate. The combined ethyl acetate layers were dried over sodium sulfate, gravity filtered, and dried in vacu to yield 5.7 g (>100%, 93% pure by LC-MS) of a red oil, 2-[2-(4,4,5,5-Tetramethyl-[l,3,2]dioxaborolan-2-yl)-5-trifluoromethoxy- benzylsulfanyl]-pyrimidine-5-carboxylic acid (4-fluoro-phenyl)-amide 6. ESI-MS m/z = 550.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ 10.52 (s, 1H), 9.11 (s, 2H), 7.81 (d, J= 8.2 Hz, 1H), 7.78-7.75 (m, 2H), 7.55 (s, 1H), 7.28-7.22 (m, 3H), 4.72 (s, 2H), 1.32 (s, 12H). The NMR spectrum also contained peaks consistent with the presence of residual DMF. The product was carried forward without further purification.
	With triethylamine In N,N-dimethyl-formamide at 20℃; for 3.75h; Inert atmosphere;	Preparation of SX-682 2-Mercapto-pyrimidine-5-carboxylic acid (4-fluoro-phenyl)-amide intermediate 2 (2.32 g, 9.3 mmol) and 2-bromomethyl-4-trifluoromethoxy-phenylboronic acid, pinacol ester (3.85 g, 10.1 mmol, Boron Molecular, Raleigh, North Carolina, USA) were suspended in anhydrous DMF (20 ml). Sonication was used to dissolve the compounds. To the reaction flask triethylamine (2.8 ml, 20.1 mmol, Sigma Aldrich, Milwaukee, Wisconsin, USA) was added and a precipitate (triethylamine-HBr) immediately formed. The reaction was layered with nitrogen gas and left to stand at room temperature for 3.75 h. The reaction was poured into H2O (500 ml) and layered with EtOAc. The biphasic solution was transferred to a separatory funnel and diluted further with EtOAc and brine. The layers were separated, and the aqueous layer was extracted twice more with EtOAc. The combined organic layers were dried over Na2SO4, gravity filtered, and dried by rotary evaporation to yield 5.7 g (98 %) of an oil, 2-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethoxy-benzylsulfanyl]-pyrimidine-5-carboxylic acid (4-fluoro-phenyl)-amide (3). 1H NMR (500 MHz, DMSO-d6) δ 10.52 (s, 1H), 9.11 (s, 2H), 7.81 (d, J = 8.2 Hz, 1H), 7.78-7.75 (m, 2H), 7.55 (s, 1H), 7.28-7.22 (m, 3H), 4.72 (s, 2H), 1.32 (s, 12H); ESI-MS (m/z): [M]+ = 550.1. The NMR spectrum also contained peaks consistent with the presence of residual DMF. The intermediate was carried forward without further purification.

5.7 g

With triethylamine In N,N-dimethyl-formamide at 20℃; for 3.75h; Sonication; Inert atmosphere;

3 Synthesis Example 3: Synthesis of pinacol ester derivative (5) 2-mercapto-pyrimidine-5-carboxylic acid (4-fluoro-phenyl) -amide intermediate (4) (2.32 g, 9.3 mmol) and 2-bromomethyl-4-trifluoromethoxy-phenylboronic acid pinacol Ester (3.85 g, 10.1 mmol)Was suspended in anhydrous DMF (20 ml).The compound was dissolved by sonication. To the reaction flask was added triethylamine (2.8 mL, 20.1 mmol) and a precipitate (triethylamine-HBr) formed immediately.The reaction was layered with nitrogen gas and left at room temperature for 3.75 hours. The reaction was poured into water (500 mL) and formed a layer with ethyl acetate.The biphasic solution was transferred to a separatory funnel and further diluted with ethyl acetate and brine. The layers were separated and the aqueous layer was extracted twice more with ethyl acetate.Combine the ethyl acetate layers, dry over sodium sulfate,5.7 g (> 100%, 93% purity by LC-MS) red oil, 2- [2- (4,4,5,5-tetramethyl- [ 1,3,2] dioxaborolan-2-yl) -5-trifluoromethoxy-benzylsulfanyl] -pyrimidine-5Carboxylic acid (4-fluoro-phenyl) -amide (6) was obtained.

Reference： [1]Current Patent Assignee: SYNTRIX BIOSYSTEMS - US2015/38461, 2015, A1 Location in patent: Paragraph 0136-0137
[2]Current Patent Assignee: SYNTRIX BIOSYSTEMS - WO2015/16938, 2015, A1 Location in patent: Paragraph 0127
[3]Lu, Xin; Horner, James W.; Paul, Erin; Shang, Xiaoying; Troncoso, Patricia; Deng, Pingna; Jiang, Shan; Chang, Qing; Spring, Denise J.; Sharma, Padmanee; Zebala, John A.; Maeda, Dean Y.; Wang, Y. Alan; Depinho, Ronald A. [Nature, 2017, vol. 543, # 7647, p. 728 - 732]
[4]Current Patent Assignee: SYNTRIX BIOSYSTEMS - JP2019/135244, 2019, A Location in patent: Paragraph 0127

4
[ 128-08-5 ]
4,4,5,5-tetramethyl-2-[2-methyl-4-(trifluoromethoxy)phenyl]-1,3,2-dioxaborolane [ No CAS ]
[ 957066-13-6 ]
C₁₄H₁₆BBr₂F₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	In acetonitrile at 20℃; for 0.25h; Flow reactor; UV-irradiation;	General procedure for continuous-flow bromination General procedure: NBS (1.87 g, 10.50 mmol, 1.05 equiv.), HPLC-grade acetonitrile, and the corresponding substrate (10 mmol) were placed into a flask and stirred until completely homogeneous. The solution was then pumped through the Corning G1 photoreactor at the desired flow rate. The reaction mixture was collected from the reactor and combined with the two separate streams of toluene and water into a 10-mL Vapourtec static mixer coil; then, the mixture was pumped into a Zaiput liquid-liquid membrane separator, the organic phase was collected and passed twice more through the Zaiput membrane separator. The organic phase was evaporated under reduced pressure, providing the corresponding brominated product.

Reference： [1]Waterford, Matthew; Saubern, Simon; Hornung, Christian H. [Australian Journal of Chemistry, 2021, vol. 74, # 8, p. 569 - 573]

5
[ 128-08-5 ]
4,4,5,5-tetramethyl-2-[2-methyl-4-(trifluoromethoxy)phenyl]-1,3,2-dioxaborolane [ No CAS ]
[ 957066-13-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	In acetonitrile at 20℃; for 0.166667h; Flow reactor; UV-irradiation;	General procedure for continuous-flow bromination General procedure: NBS (1.87 g, 10.50 mmol, 1.05 equiv.), HPLC-grade acetonitrile, and the corresponding substrate (10 mmol) were placed into a flask and stirred until completely homogeneous. The solution was then pumped through the Corning G1 photoreactor at the desired flow rate. The reaction mixture was collected from the reactor and combined with the two separate streams of toluene and water into a 10-mL Vapourtec static mixer coil; then, the mixture was pumped into a Zaiput liquid-liquid membrane separator, the organic phase was collected and passed twice more through the Zaiput membrane separator. The organic phase was evaporated under reduced pressure, providing the corresponding brominated product.

Reference： [1]Waterford, Matthew; Saubern, Simon; Hornung, Christian H. [Australian Journal of Chemistry, 2021, vol. 74, # 8, p. 569 - 573]

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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 957066-13-6 ] {[proInfo.proName]}

Quality Control of [ 957066-13-6 ]

Related Doc. of [ 957066-13-6 ]

Product Details of [ 957066-13-6 ]

Safety of [ 957066-13-6 ]

Application In Synthesis of [ 957066-13-6 ]

[ 957066-13-6 ] Synthesis Path-Downstream 1~5

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