[ CAS No. 1218790-40-9 ] {[proInfo.proName]}

Name: 1218790-40-9|4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole|98%
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Quality Control of [ 1218790-40-9 ]

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Product Details of [ 1218790-40-9 ]

CAS No. :	1218790-40-9	MDL No. :	MFCD11501039
Formula :	C₁₀H₁₄BF₃N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WHYPQJYBTNZKBY-UHFFFAOYSA-N
M.W :	262.04	Pubchem ID :	45933666
Synonyms :

Safety of [ 1218790-40-9 ]

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

Application In Synthesis of [ 1218790-40-9 ]

* 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 [ 1218790-40-9 ]

[ 1218790-40-9 ] Synthesis Path-Downstream 1~27

1
[ 5305-59-9 ]
[ 1218790-40-9 ]
[ 1263400-56-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate In tetrahydrofuran; water at 90℃; Inert atmosphere;	18.A A mixture of 6-chloropyrimidin-4-amine (260.0 mg, 2.0 mmol), 4-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole (0.66 mL, 3.0 mmol), (Ph3P)2PdCl2 (70.2 mg, 0.1 mmol), Na2CO3 (1.48 g, 14 mmol) in 8.0 mL of THF and 2.0 mL of H2O was degassed and purged with nitrogen, then heated at 90°C overnight. The reaction mixture was partitioned between EtOAc and brine, the combined organic extracts were dried (Na2SO4), concentrated in vacuo, followed by chromatography (EtOAc/ Hexanes: 0-30%) to afford 6-(3-(trifluoromethyl)-1H-pyrazol-4-yl)pyrimidin-4-amine. ESI-MS ml z 230.1 (MH+).

Reference： [1]Current Patent Assignee: IRM LLC - WO2011/14515, 2011, A1 Location in patent: Page/Page column 116

2
[ 1218790-40-9 ]
[ 1268867-67-9 ]
methyl 3-(isopropyl(methyl)amino)-2-(3-(trifluoromethyl)-1H-pyrazol-4-yl)quinoxaline-6-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With sodium carbonate In 1,2-dimethoxyethane; water at 90℃; for 0.5h; Inert atmosphere;	9.1 Step 1. Methyl 3-(isopropyl(methyl)amino)-2-(3-(trifluoromethyl)-7H-pyrazol-4- yl)quinoxaline-6-carboxylateTo a solution of 4-(4, 4, 5, 5-tetramethyl-l , 3, 2-dioxaborolan-2-yl)-3-(trifluoromethyl)-7H- pyrazole (536.0 mg, 2.05 mmol) in DME (5 mL) and water (0.5 mL) was added methyl 2- chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (200.0 mg, 0.68 mmol), sodium carbonate (217.0 mg, 2.05 mmol) and Pd(PPh3)4 (39 mg, 0.03 mmol) with stirring for 0.5 h at 90°C in an oil bath with an inert atmosphere of nitrogen. The reaction mixture was concentrated under vacuum to get a residue, which was purified by a silica gel column with 2% - 10% ethyl acetate in petroleum to afford methyl 3-(isopropyl (methyl) amino)-2-(3- (trifluoromethyl)-7H-pyrazol-4-yl) quinoxaline-6-carboxylate as a light yellow solid (80 mg, 30%).LC/MS (ES, m/z): [M+H]+ 394.0'H-NMR (300 MHz, CDC13): δ 8.54 (d, / = 1.8 Hz, 1H), 8.08 - 8.14 (m, 2H), 7.98 (d, / = 8.7 Hz, 1H), 4.13 - 4.24 (m, 1H), 4.01 (s, 3H), 2.76 (s, 3H), 1.13 (d, / = 6.6 Hz, 6H)

Reference： [1]Current Patent Assignee: SYNERGENICS LCC - WO2012/119046, 2012, A2 Location in patent: Page/Page column 50-51

3
[ 1218790-40-9 ]
[ 1282518-61-9 ]
[ 1401304-23-1 ]

Yield	Reaction Conditions	Operation in experiment
3%	With caesium carbonate In 1,4-dioxane; water at 80 - 85℃; for 42h; Inert atmosphere;	159.1 A mixture of 9-bromo-2-iodo-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene (750 mg, 1.91 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-trifluoromethyl-1H-pyrazole (550 mg, 2.10 mmol), PdCl2dppf.DCM (156 mg, 0.19 mmol) and Cs2CO3 (1.55 g, 4.77 mmol) in dioxane (12 mL) and H2O (3 mL) was purged with argon and heated at 80° C. for 18 h. Further 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-trifluoromethyl-1H-pyrazole (225 mg, 1.05 mmol) and PdCl2dppf.DCM (78 mg, 0.09 mmol) were added and the mixture heated at 85° C. for a further 24 h. The reaction mixture was loaded onto an Isolute SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH. The resulting residue was purified by column chromatography (Si-PCC, gradient 0-5% MeOH in DCM) affording 9-Bromo-2-(3-trifluoromethyl-1H-pyrazol-4-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene as a white solid (20 mg, 3%). LCMS: RT 4.42 min [M+H]+ 399.0 and 401.0. 1H NMR (CDCl3, 400 MHz): δ 13.65 (1H, s), 8.57 (1H, d, J=2.61 Hz), 8.30 (1H, s), 7.43-7.42 (2H, m), 7.00 (1H, d, J=8.71 Hz), 4.52-4.45 (4H, m)

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2012/245144, 2012, A1 Location in patent: Page/Page column 150

4
[ 1218790-40-9 ]
8-bromo-4-methyl-2-phenyl-4H-pyrazolo[1,5-a]quinazolin-5-one [ No CAS ]
4-methyl-2-phenyl-8-(3-trifluoromethyl-1H-pyrazol-4-yl)-4H-pyrazolo[1,5-a]quinazolin-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 150℃; for 1h; Microwave irradiation; Inert atmosphere;	19 General procedure IV: Formation of example I from 4H-Pyrazolo[1 ,5-a]quinazolin-5-one F or D and boronic acid derivatives G or from 4H-Pyrazolo[1 ,5-a]quinazolin-5-one J and bromide K (cf. Scheme 1 and 2) or from 4H-Pyrolo[1 ,5-a]quinazolin-5-one P and boronic acid derivatives G (cf. Scheme 3) Method (i): under microwave irradiation General procedure: Under inert atmosphere, a mixture of halide F, D, K or P (1.0 equiv.), boronic acid derivative R1-M G or J (1.5 equiv.), PdCI2(dppf)2 (0.1 equiv.) and aqueous NaHCO3 (1.2 M- 3.0 equiv.) in DMF (C=0.1 molL-1) was submitted to microwave irradiation (120°C, 10 min, P< 70W). The reaction mixture was hydrolysed, and then extracted with EtOAc twice. The organic layers were combined, washed with brine, dried over MgSO4, concentrated and purified to afford the product. Example 19 was obtained according to general procedure IV(i) starting from compound 3 in presence 3-trifluoromethyl-1H-pyrazole-4-boronica cid pinacol ester. The reaction mixture was submitted to microwave irradiation for 1 Hr at 150°C. Purification by flash-chromatography (AcOEtin cyclohexane, 60%) afforded example 19 as a white solid in 82% yield. 1H-NMR (400 MHz, DMSO): 3.59 (s, 3H, N-CH3); 6.84 (s, 1H, Ar); 7.41-7.53 (m, 3H, Ar); 7.59 (dd, J 8.3 Hz, J 1.6 Hz, 1H, Ar); 7.99-8.01 (m, 2H, Ar); 8.23 (d, J 8.3 Hz, 1H, Ar); 8.25 (d, J1.6 Hz, 1H, Ar); 8.54 (bs, 1H, Ar); 14.01 (bs, 1H, NH). M/Z (M+H]+ = 410.1. MP: >250°C.

Reference： [1]Current Patent Assignee: DOMAIN THERAPEUTICS SA - WO2013/174822, 2013, A1 Location in patent: Page/Page column 71; 72; 80

5
[ 866638-72-4 ]
[ 73183-34-3 ]
[ 1218790-40-9 ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In N,N-dimethyl-formamide at 90℃; for 2h;	31.2 Step 2: Preparation of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole Step 2: Preparation of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole To a mixture of 4-iodo-3-(trifluoromethyl)-1H-pyrazole (100 mg, 0.38 mmol) and (4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (397 mg, 0.57 mmol) in DMF (3 mL) were added 1,1'-bis-(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (31 mg, 0.04 mmol) and potassium acetate (509 mg, 0.76). The reaction mixture was stirred at 90° C. for 2 hr, then quenched with water and extracted with Et2O. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrated to afford 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole. LC-MS: m/z 263 (M+H)+.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In N,N-dimethyl-formamide at 90℃; for 2h;	31.2 Step 2: Preparation of 4-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3 -(trfluoromethyl) -1 Hpyrazole. Step 2: Preparation of 4-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3 -(trfluoromethyl) -1 Hpyrazole. To a mixture of 4-iodo-3-(trifluoromethyl)-1H-pyrazole (100 mg, 0.38 mmol) and (4,4,4’,4’,5,5,5’,5’-octamethyl-2,2’-bi(1,3,2-dioxaborolane) (397 mg, 0.57 mmol) in DIVIF (3 mL) were added 1,1 ‘-bis -(diphenylphosphino)ferrocene-palladium(ll)dichloride dichloromethane complex (31 mg, 0.04 mmol) and potassium acetate (509 mg, 0.76).The reaction mixture was stirred at 90 °C for 2 hr, then quenched with water and extracted with Et20. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrated to afford 4-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)-3 -(trifluoromethyl)- 1 H-pyrazole.LC-MS: m/z263 (M+H).

Reference： [1]Current Patent Assignee: SERVIER MONDE - US2015/18328, 2015, A1 Location in patent: Paragraph 1302
[2]Current Patent Assignee: SERVIER MONDE - WO2015/3640, 2015, A1 Location in patent: Page/Page column 284; 285

6
[ 1218790-40-9 ]
6-chloro-N²,N⁴-bis(4,4-difluorocyclohexyl)-1,3,5-triazine-2,4-diamine [ No CAS ]
N<SUP>2</SUP>,N<SUP>4</SUP>-bis (4,4-difluorocyclohexyl)-6-(3-(trifluoromethyl)-1H-pyrazol-4-yl)-1,3,5-triazine-2,4-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 16h; Inert atmosphere;	31.3 Step 3: Preparation of N²,N⁴-bis(4,4-difluorocyclohexyl)-6-(3-(trifluoromethyl)-1H-pyrazol-4-yl)-1,3,5-triazine-2,4-diamine Step 3: Preparation of N2,N4-bis(4,4-difluorocyclohexyl)-6-(3-(trifluoromethyl)-1H-pyrazol-4-yl)-1,3,5-triazine-2,4-diamine To a solution of 6-chloro-N2,N4-bis(4,4-difluorocyclohexyl)-1,3,5-triazine-2,4-diamine (145 mg, 0.38 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole (100 mg, 0.38 mmol) in DME (3 mL) and H2O (1 mL) were added K2CO3 (158 mg, 1.15 mmol) and Pd(PPh3)4 (44 mg, 0.04 mmol) under N2 atmosphere. The mixture was stirred at 90° C. for 16 hr, and then filtered. The filtrate was partitioned between EtOAc and H2O. The aqueous layer was separated and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrated and purified by standard methods to afford N2,N4-bis(4,4-difluorocyclohexyl)-6-(3-(trifluoromethyl)-1H-pyrazol-4-yl)-1,3,5-triazine-2,4-diamine. 1H NMR (400 MHz, DMSO-d6) δ 8.09-7.47 (m, 3H), 7.29-7.00 (m, 1H), 4.11-3.76 (m, 2H), 2.19-1.46 (m, 16H). LC-MS: m/z 482 (M+H)+.
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 16h; Inert atmosphere;	31.3 Step 3: Preparation of N2,N’-bis (4,4-dfluorocyclohexyl)-6-(3-(truoromethyl)-1H-pyrazol-4- yl)-1,3,5-triazine-2,4-diamine. Step 3: Preparation of N2,N’-bis (4,4-dfluorocyclohexyl)-6-(3-(truoromethyl)-1H-pyrazol-4- yl)-1,3,5-triazine-2,4-diamine. To a solution of 6-chloro-N2,N4-bis(4,4-difluorocyclohexyl)- 1,3 ,5-triazine-2,4-diamine (145 mg, 0.38 mmol) and 4-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole (100 mg, 0.38 mmol) in DME (3 mL) and 1120 (1 mL) were added K2C03 (158 mg, 1.15 mmol) and Pd(PPh3)4 (44 mg, 0.04 mmol) under N2 atmosphere. The mixture was stirred at 90°C for 16 hr, and then filtered. The filtrate was partitioned between EtOAc and 1120. The aqueous layer was separated and extracted with EtOAc. The combined organic layerswere washed with brine, dried over anhydrous Na2SO4, and concentrated and purified by standard methods to afford N2,N4-bis(4,4-difluorocyclohexyl)-6-(3- (trifluoromethyl)- 1 H-pyrazol-4-yl)- 1,3,5 -triazine-2,4-diamine.‘H NMR (400 MHz, DMSO-d6) 8.09-7.47 (m, 311), 7.29-7.00 (m, 111), 4.11 -3.76 (m, 211), 2.19 - 1.46 (m, 1611).LC-MS: m/z 482 (M+H).

Reference： [1]Current Patent Assignee: SERVIER MONDE - US2015/18328, 2015, A1 Location in patent: Paragraph 1303-1304
[2]Current Patent Assignee: SERVIER MONDE - WO2015/3640, 2015, A1 Location in patent: Page/Page column 284; 285

7
[ 1218790-40-9 ]
[ 591769-05-0 ]
C₁₈H₂₅BF₃N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 80℃; for 8h;Inert atmosphere;	Compound 17 (190mg, 0.7mmol) and Compound 2 (169mg, 1.4mmol) placed in 50mL single-neck flask under nitrogen, a solution of DBU (425mg, 2.8mmol) at room temperature and mix well. Then heated to 80 , reaction 8h. After completion of the reaction, the solvent spin dry column chromatography (ethyl acetate: petroleum ether = 5: 1) to give a colorless oil 60mg, 17percent yield.

Reference： [1]Patent: CN105218548,2016,A .Location in patent: Paragraph 0086; 0087; 0088; 0089

8
[ 1218790-40-9 ]
(±)-trans-N-(6-bromo-8-chloroisoquinolin-3-yl)-2-cyanocyclopropanecarboxamide [ No CAS ]
(±)-trans-N-[8-chloro-6-[3-(trifluoromethyl)-1H-pyrazol-4-yl]-3-isoquinolyl]-2-cyanocyclopropanecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 100℃; for 3h;	63.1 Step 1: (±)-trans-N-[8-chloro-6-[3-(trifluoromethyl)-1H-pyrazol-4-yl]-3-isoquinolyl]-2-cyano-cyclopropanecarboxamide A mixture of (±)-trans-N-(6-bromo-8-chloro-3-isoquinolyl)-2-cyano-cyclopropanecarboxamide (350 mg, 1 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole (300 mg, 1.14 mmol), Pd(dppf)Cl2 (70 mg, 0.1 mmol), potassium phosphate (3 H2O) (660 mg, 2.48 mmol) in 1,4-dioxane (9 mL) and water (1.5 mL) was stirred at 100° C. for 3 h. The reaction was concentrated to dryness. The crude residue was then purified by silica gel column chromatography (ethyl acetate/petroleum etherl/13-1/1) to afford (±)-trans-N-[8-chloro-6-[3-(trifluoromethyl)-1H-pyrazol-4-yl]-3-isoquinolyl]-2-cyano-cyclopropanecarboxamide (230 mg, 51% yield) as a white solid. LCMS (ESI): [M+H]+=406.1

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2018/282282, 2018, A1 Location in patent: Paragraph 1071; 1072

9
[ 1218790-40-9 ]
benzyl-3-(4-methoxyphenyl)-3-(3-methyl-4-(((trifluoromethyl)sulfonyl)oxy)phenyl)azetidine-1-carboxylate [ No CAS ]
benzyl 3-(4-methoxyphenyl)-3-(3-methyl-4-(3-(trifluoromethyl)-1H-pyrazol-4-yl)phenyl)azetidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,2-dimethoxyethane; water at 100℃; for 25h; Sealed tube;

Reference： [1]Denis, Camille; Dubois, Maryne A.J.; Voisin-Chiret, Anne Sophie; Bureau, Ronan; Choi, Chulho; Mousseau, James J.; Bull, James A. [Organic Letters, 2019, vol. 21, # 1, p. 300 - 304]

10
[ 1218790-40-9 ]
N-((1S,2R)-2-(3-bromo-6-fluoro-2-methylphenyl)-1-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)propyl)-4-chloro-2-methoxybenzenesulfonamide [ No CAS ]
4-chloro-N-((1S,2R)-2-(6-fluoro-2-methyl-3-(3-(trifluoromethyl)-1H-pyrazol-4-yl)phenyl)-1-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)propyl)-2-methoxybenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate In 1,4-dioxane; water at 100℃; for 1h;	316 (Step 2) General procedure: To a 1,4-dioxane (1.0 mL) solution of N-((1S,2R)-2-(3-bromo-6-fluoro-2-methylphenyl)-1-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)propyl)-4-chloro-2-methoxybenzenesulfonamide (11 mg), 4-methoxyphenylboronic acid (5.0 mg),[1,1’-bis (diphenylphosphino) ferrocene] palladium (II) dichloride dichloromethane adduct (4.0 mg), and a sodium carbonateaqueous solution (2 M, 100 mL) was added sequentially at room temperature, and the reaction solution wasstirred at 100 ° C for 1 hour. The reaction solution was allowed to cool to room temperature, insoluble matter was removedby CELITE filtration, and the residue was washed with hexane / ethyl acetate = 1/1 (10 mL). The combined filtrate wasconcentrated under reduced pressure, and the obtained residue was purified by reverse phase HPLC (water / acetonitrile)to give the title compound.

Reference： [1]Current Patent Assignee: OTSUKA HOLDINGS CO LTD - EP3466934, 2019, A1 Location in patent: Paragraph 0496; 0497

11
[ 1218790-40-9 ]
benzyl 3-((4-bromophenyl)thio)-3-(4-methoxyphenyl)azetidine-1-carboxylate [ No CAS ]
benzyl 3-(4-methoxyphenyl)-3-((4-(3-(trifluoromethyl)-1H-pyrazol-4-yl)phenyl)thio)azetidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,2-dimethoxyethane; water at 100℃; for 18h; Inert atmosphere;

Reference： [1]Dubois, Maryne A.J.; Lazaridou, Anna; Choi, Chulho; Mousseau, James J.; Bull, James A. [Journal of Organic Chemistry, 2019, vol. 84, # 9, p. 5943 - 5956]

12
[ 1218790-40-9 ]
6-[(6-chloropyridin-3-yl)methyl]-5-methyl-[1,2,5]oxadiazolo[3,4-b]pyridin-7-amine [ No CAS ]
5-methyl-6-({6-[3-(trifluoromethyl)-1H-pyrazol-4-yl]pyridin-3-yl}methyl)-[1,2,5]oxadiazolo[3,4-b]pyridin-7-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3 mg	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 150℃; for 0.5h; Microwave irradiation;	12 5-methyl-6-[3-(1H-pyrazol-5-yl)phenyl]methyl}-[1,2,5]oxadiazolo[3,4-b]pyridin-7-amine General procedure: To a mixture of compound 2.6 6-[(3-Bromophenyl)methyl]-5-methyl-[1 ,2,5]oxadiazolo[3,4-b]pyridin-7-amine (50.0 mg; 0.16 mmol) and 1 H-Pyrazol-3-yl boronic acid (26.3 mg; 0.24 mmol) in 1.5 ml_ dioxane sodium carbonate (2M aqueous solution; 1.00 ml_) is added. Thereafter 1 ,1 '-bis(diphenylphosphino)ferrocene- dichloropalladium(ll) (7.50 mg; 0.07 mmol) is added and the mixture is stirred at 150°C for 30 minutes in a microwave. The mixture is diluted with water and extracted three times with dichloromethane. The combined organic layers are dried and concentrated under reduced pressure. The residue is purified by reverse phase chromatography-HPLC (modifier: trifluoroacetic acid).Yield: 43.0 mg (90 % of theory)Mass spectrometry (ESI+): m/z = 307 [M+H]+HPLC (Method 3): Retention time = 0.810 min.

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2019/149657, 2019, A1 Location in patent: Page/Page column 162; 167

13
[ 1218790-40-9 ]
6-({7-amino-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl}methyl)-3-bromopyridin-2-amine [ No CAS ]
6-({7-amino-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl}methyl)-3-[3-(trifluoromethyl)-1H-pyrazol-4-yl]pyridin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 120℃; for 1h;	16.B Step B Example 16.1 6-({7-Amino-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl}methyl)-3-[3-(trifluoromethyl)-1H- pyrazol-4-yl]pyridin-2-amine The reaction is carried out under an argon atmosphere. To a mixture of 6-({7-amino-5- methyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl}methyl)-3-bromopyridin-2-amine (50.0 mg; 0.15 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole (66.6 mg; 0.25 mmol), potassium carbonate (2M aqueous solution) (200 µL; 0.40 mmol) in 2 mL of dioxane is added 1,1'-bis(di-tert-butylphosphino)ferrocene palladium dichloride (29.2 mg; 44.9 µmol) and the reaction is stirred for 1 hour at 120°C. The reaction is quenched with methanol, filtered and purified by reverse phase chromatography-HPLC (modifier: ammonium hydroxide) (0625) Yield: 7 mg (12 % of theory) (0626) Mass spectrometry (ESI+): m/z = 390 [M+H]+ (0627) HPLC (Method 1): Retention time = 0.716 min.

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2019/149660, 2019, A1 Location in patent: Page/Page column 100

14
[ 1218790-40-9 ]
C₂₃H₂₃F₃N₄O₅S [ No CAS ]
(S)-2-(1-(4-methoxypyridin-2-yl)ethyl)-7-((2-methyl-1H-imidazol-1-yl)methyl)-5-(3-(trifluoromethyl)-1H-pyrazol-4-yl)-3,4-dihydroisoquinolin-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; water at 80℃; for 14h;	237 Step B. Preparation of methyl 2-((4-methoxypyridin-2-yl)methyl)-5-(l-methyl-3- (trifluoromethyl)-l/ -pyrazol-4-yl)-l-oxo-l,2,3,4-tetrahydroisoquinoline-7-carboxylate. General procedure: Pd(PPh3)4 (0.16 g, 0.14 mmol, 0.04 equiv) and potassium carbonate (2.9 g, 8.9 mmol, 2.5 equiv) were added to a solution of methyl 2-((4-methoxypyridin-2-yl)methyl)-l-oxo-5- (((trifluoromethyl)sulfonyl)oxy)-l,2,3,4-tetrahydroisoquinoline-7-carboxylate (1.7 g, 3.5 mmol, 1 equiv) and (1 -methyl-3 -(trifluorom ethyl)- l/7-pyrazol-4-yl)boronic acid (0.8 g,4.1 mmol, 1.2 equiv) in dioxane/H20 (83 mL, 0.04 M,4: 1) and degassed for 20 min. The reaction mixture was then placed in a preheated heating block and stirred for 14 h at 80 °C. At 23 °C, brine was added to the mixture and extracted with EtOAc (3x 40 mL). The combined organic layers were dried over NaiSOi and concentrated in vacuo. The residue was purified by flash chromatography (Combi-flash Rf, DCM/MeOH = 0-3% gradient) to afford the title compound (1.5 g, 3.2 mmol, 90%) as a tan solid. NMR (400 MHz, Chloroform-7) d 8.82 (d, J= 1.9 Hz, 1H), 8.34 (d, j= 5.8 Hz, 1H), 8.02 (d, j= 1.9 Hz, 1H), 7.37 (d, 7= 1.1 Hz, 1H), 6.92 (d, J= 2.5 Hz, 1H), 6.73 (dd, 7 = 5.8, 2.5 Hz, 1H),4.85 (s, 2H),4.01 (s, 3H), 3.92 (s, 3H), 3.83 (s, 3H), 3.59 (t, J= 6.6 Hz, 2H), 2.82 (t, J= 6.5 Hz, 2H); 19F NMR (376 MHz, Chloroform-7) d -60.28; LC-MS: >95% (215, 254 nm), Rx = 0.089 min, MS (ES) 475 [M+H]+.

Reference： [1]Current Patent Assignee: VANDERBILT UNIVERSITY - WO2020/86857, 2020, A1 Location in patent: Paragraph 00149; 00527

15
[ 1218790-40-9 ]
3-(4-(((trifluoromethyl)sulfonyl)oxy)phenyl)oxetane-3-carboxylic acid [ No CAS ]
3-(4-(3-(trifluoromethyl)-1H-pyrazol-4-yl)phenyl)oxetane-3-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,2-dimethoxyethane; water at 90℃; Inert atmosphere;

Reference： [1]Bull, James A.; Choi, Chulho; Dubois, Maryne A. J.; Lee Wei Jie, Alvin; Mousseau, James J.; Smith, Milo A.; White, Andrew J. P. [Organic Letters, 2020, vol. 22, # 14, p. 5279 - 5283]

16
[ 1218790-40-9 ]
[ 590-17-0 ]
2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-pyrazol-1-yl]acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 4h;	828.4 Step 4: 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetonitrile To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole (260 mg, 1.0 mmol, Eq: 1) and DIPEA (258 mg, 2.0 mmol, Eq: 2) in DCM (10 mL) was added 2- bromoacetonitrile (144 mg, 1.2 mmol, , Eq: 1.2) and then stirred at room temperature for 4 hr. The mixture was poured into water and then extracted with dichloromethane, the organic layer was concentrated and purified by silica column to afford the title compound (250 mg, 83%). MS(m/e): 302.1 (M+H).
83%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 4h;	828.4 Step 4: 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetonitrile To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole (260 mg, 1.0 mmol, Eq: 1) and DIPEA (258 mg, 2.0 mmol, Eq: 2) in DCM (10 mL) was added 2- bromoacetonitrile (144 mg, 1.2 mmol, , Eq: 1.2) and then stirred at room temperature for 4 hr. The mixture was poured into water and then extracted with dichloromethane, the organic layer was concentrated and purified by silica column to afford the title compound (250 mg, 83%). MS(m/e): 302.1 (M+H).
950 mg	With potassium carbonate In acetonitrile at 25℃; for 16h;	60.7 Step 7: 2-[4-(4,4,5,5-Tetramethyl-l,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyrazol-l-yl]acetonitrile mixture of 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-lH-pyrazole (0.8 g, 3.05 mmol, 1 eq), bromoacetonitrile (0.44 g, 3.66 mmol, 1.2 eq), potassium carbonate (843.8 mg,6.11 mmol, 2 eq) in ACN (10 mL) was stirred at 25 °C for 16 h. The mixture was filtered and concentrated to give a crude product, wH-ich was further purified with column chromatography (PE/EA=100: 1 to 20:1) to afford 2-[4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)-3-(trifluoromethyl)pyrazol-l-yl]acetonitrile (950 mg) as a colorless oil. MS (ESI, m/z): 301.9 [M+H]+

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2021/219578, 2021, A1 Location in patent: Page/Page column 410-411
[2]Current Patent Assignee: ROCHE HOLDING AG - WO2021/219578, 2021, A1 Location in patent: Page/Page column 410-411
[3]Current Patent Assignee: ROCHE HOLDING AG - WO2020/182648, 2020, A1 Location in patent: Page/Page column 136; 138-139

17
[ 1218790-40-9 ]
[ 1049677-32-8 ]
8-chloro-3-[3-(trifluoromethyl)-1H-pyrazol-4-yl]imidazo[1,2-a]pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate In 1,4-dioxane; water at 105℃; for 5h;	4.1 Step 1: 8-chloro-3-[3-(trifluoromethyl)-1H-pyrazol-4-yl]imidazo[1,2-a]pyrazine A mixture of 8-chloro-3-iodoimidazo[1,2-a]pyrazine (3 g, 10.7 mmol), 4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole (3.38 g, 12.9 mmol), 1,1'- bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane adduct (877 mg, 1.07 mmol,) and Na2CO3 (2.28 g, 21.5 mmol) in dioxane (107 mL) / water (10.7 mL) was stirred for 5 h at 105 °C. The crude material was absorbed with Isolute HM-N, dried and purified by flash chromatography to afford 8- chloro-3-(3-(trifluoromethyl)-1H-pyrazol-4-yl)imidazo[1,2-a]pyrazine as an off-white solid (1.76 g, 6.12 mmol, 57 % yield) . MS(m/e): 288.2 (M+H).
57%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate In 1,4-dioxane; water at 105℃; for 5h;	4.1 Step 1: 8-chloro-3-[3-(trifluoromethyl)-1H-pyrazol-4-yl]imidazo[1,2-a]pyrazine A mixture of 8-chloro-3-iodoimidazo[1,2-a]pyrazine (3 g, 10.7 mmol), 4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole (3.38 g, 12.9 mmol), 1,1'- bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane adduct (877 mg, 1.07 mmol,) and Na2CO3 (2.28 g, 21.5 mmol) in dioxane (107 mL) / water (10.7 mL) was stirred for 5 h at 105 °C. The crude material was absorbed with Isolute HM-N, dried and purified by flash chromatography to afford 8- chloro-3-(3-(trifluoromethyl)-1H-pyrazol-4-yl)imidazo[1,2-a]pyrazine as an off-white solid (1.76 g, 6.12 mmol, 57 % yield) . MS(m/e): 288.2 (M+H).

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2021/219578, 2021, A1 Location in patent: Page/Page column 116-117
[2]Current Patent Assignee: ROCHE HOLDING AG - WO2021/219578, 2021, A1 Location in patent: Page/Page column 116-117

18
[ 1218790-40-9 ]
methyl 2-chloro-4-[(3-iodoimidazo[1,2-a]pyrazin-8-yl)amino]benzoate [ No CAS ]
methyl 2-chloro-4-[[3-[3-(trifluoromethyl)-1H-pyrazol-4-yl]imidazo[1,2-a]pyrazin-8-yl]amino]benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19.63%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 25 - 90℃; for 12h; Inert atmosphere;	58.2; 108.1 Methyl 2-chloro-4-[[3-[3-(trifluoromethyl)-1H-pyrazol-4-yl]imidazo[1,2-a]pyrazin-8- yl]amino]benzoate To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole (1.59 g, 6.07 mmol, 1.3 eq) in water (115 mL)/1,4-dioxane (115 mL) was added methyl 2- chloro-4-[(3-iodoimidazo[1,2-a]pyrazin-8-yl)amino]benzoate (2 g, 4.67 mmol, 1 eq), 1,1'- bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (1.14 g, 1.4 mmol, 0.300 eq) and sodium carbonate (1.48 g, 14 mmol, 3 eq) at 25 °C. The reaction mixture was stirred at 90 °C for 12 h under N2. The reaction was poured into water (100 ml) and extracted with DCM (50 ml x 3). The organic phase was combined and concentrated under reduce pressure. The target compound was purified by silica chromatography column (PE: EtOAc=50:1 to 1:1) to afford the title compound (0.400 g, 0.920 mmol, 19.63% yield) as a dark green solid. MS (ESI, m/z): 437.0 [M+H]+.
19.63%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 25 - 90℃; for 12h; Inert atmosphere;	58.2; 108.1 Methyl 2-chloro-4-[[3-[3-(trifluoromethyl)-1H-pyrazol-4-yl]imidazo[1,2-a]pyrazin-8- yl]amino]benzoate To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole (1.59 g, 6.07 mmol, 1.3 eq) in water (115 mL)/1,4-dioxane (115 mL) was added methyl 2- chloro-4-[(3-iodoimidazo[1,2-a]pyrazin-8-yl)amino]benzoate (2 g, 4.67 mmol, 1 eq), 1,1'- bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (1.14 g, 1.4 mmol, 0.300 eq) and sodium carbonate (1.48 g, 14 mmol, 3 eq) at 25 °C. The reaction mixture was stirred at 90 °C for 12 h under N2. The reaction was poured into water (100 ml) and extracted with DCM (50 ml x 3). The organic phase was combined and concentrated under reduce pressure. The target compound was purified by silica chromatography column (PE: EtOAc=50:1 to 1:1) to afford the title compound (0.400 g, 0.920 mmol, 19.63% yield) as a dark green solid. MS (ESI, m/z): 437.0 [M+H]+.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2021/249896, 2021, A1 Location in patent: Page/Page column 51; 120-121; 199-200
[2]Current Patent Assignee: ROCHE HOLDING AG - WO2021/249896, 2021, A1 Location in patent: Page/Page column 51; 120-121; 199-200

19
[ 1218790-40-9 ]
tert-butyl 4-[2-chloro-4-[(3-iodoimidazo[1,2-a]pyrazin-8-yl)amino]benzoyl]piperazine-1-carboxylate [ No CAS ]
tert-butyl 4-[2-chloro-4-[[3-[3-(trifluoromethyl)-1H-pyrazol-4-yl]imidazo[1,2-a]pyrazin-8-yl]amino]benzoyl]piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36.82%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 25 - 90℃; for 12h; Inert atmosphere;	62.4 tert-Butyl 4-[2-chloro-4-[[3-[3-(trifluoromethyl)-1H-pyrazol-4-yl]imidazo[1,2-a]pyrazin-8- yl]amino]benzoyl]piperazine-1-carboxylate To a solution of tert-butyl 4-[2-chloro-4-[(3-iodoimidazo[1,2-a]pyrazin-8- yl)amino]benzoyl]piperazine-1-carboxylate (3 g, 5.15 mmol, 1 eq) in water (9 mL)/1,4-dioxane (90 mL) was added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H- pyrazole (1.75 g, 6.69 mmol, 1.3 eq), 1,1'-bis(diphenylphosphino)ferrocene- palladium(II)dichloride dichloromethane complex (0.42 g, 0.510 mmol, 0.1 eq) and sodium carbonate (1637 mg, 15.44 mmol, 3 eq) at 25 °C. The mixture was stirred at 90 °C for 12 h under N2. The reaction mixture was poured into water (100 ml) and extracted with EtOAc (50 ml x 3). The organic phase was combined and concentrated under reduced pressure and then purified by silica chromatography column (PE: EtOAc=1:1 to EtOAc) to afford the title compound (1.4 g, 2.37 mmol, 36.82% yield) as a light brown solid. MS (ESI, m/z): 591.1 [M+H]+.
36.82%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 25 - 90℃; for 12h; Inert atmosphere;	62.4 tert-Butyl 4-[2-chloro-4-[[3-[3-(trifluoromethyl)-1H-pyrazol-4-yl]imidazo[1,2-a]pyrazin-8- yl]amino]benzoyl]piperazine-1-carboxylate To a solution of tert-butyl 4-[2-chloro-4-[(3-iodoimidazo[1,2-a]pyrazin-8- yl)amino]benzoyl]piperazine-1-carboxylate (3 g, 5.15 mmol, 1 eq) in water (9 mL)/1,4-dioxane (90 mL) was added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H- pyrazole (1.75 g, 6.69 mmol, 1.3 eq), 1,1'-bis(diphenylphosphino)ferrocene- palladium(II)dichloride dichloromethane complex (0.42 g, 0.510 mmol, 0.1 eq) and sodium carbonate (1637 mg, 15.44 mmol, 3 eq) at 25 °C. The mixture was stirred at 90 °C for 12 h under N2. The reaction mixture was poured into water (100 ml) and extracted with EtOAc (50 ml x 3). The organic phase was combined and concentrated under reduced pressure and then purified by silica chromatography column (PE: EtOAc=1:1 to EtOAc) to afford the title compound (1.4 g, 2.37 mmol, 36.82% yield) as a light brown solid. MS (ESI, m/z): 591.1 [M+H]+.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2021/249896, 2021, A1 Location in patent: Page/Page column 51; 129-130
[2]Current Patent Assignee: ROCHE HOLDING AG - WO2021/249896, 2021, A1 Location in patent: Page/Page column 51; 129-130

20
[ 1218790-40-9 ]
[ 76513-69-4 ]
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93.5%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;	138.1 Trimethyl-[2-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyrazol-1- yl]methoxy]ethyl]silane In a 100 mL round-bottomed flask, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3- (trifluoromethyl)-1 h-pyrazole (500 mg, 1.91 mmol ), SEM-Cl (414 mg, 440 µl, 2.48 mmol ) and DIPEA (740 mg, 1000 µl, 5.72 mmol ) were combined with DCM (20 mL) to give a colorless solution. The reaction was stirred at room temperature for 2 h. The crude reaction mixture was concentrated in vacuum.The crude material was purified by flash chromatography (silica gel, 40 g, 0% to 60% DCM in PE) to afford the title compound (700 mg, 1.78 mmol, 93.5 % yield). MS (ESI, m/z): 393.1 [M+H]+
93.5%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;	138.1 Trimethyl-[2-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyrazol-1- yl]methoxy]ethyl]silane In a 100 mL round-bottomed flask, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3- (trifluoromethyl)-1 h-pyrazole (500 mg, 1.91 mmol ), SEM-Cl (414 mg, 440 µl, 2.48 mmol ) and DIPEA (740 mg, 1000 µl, 5.72 mmol ) were combined with DCM (20 mL) to give a colorless solution. The reaction was stirred at room temperature for 2 h. The crude reaction mixture was concentrated in vacuum.The crude material was purified by flash chromatography (silica gel, 40 g, 0% to 60% DCM in PE) to afford the title compound (700 mg, 1.78 mmol, 93.5 % yield). MS (ESI, m/z): 393.1 [M+H]+

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2021/249896, 2021, A1 Location in patent: Page/Page column 51; 259
[2]Current Patent Assignee: ROCHE HOLDING AG - WO2021/249896, 2021, A1 Location in patent: Page/Page column 51; 259

21
[ 1218790-40-9 ]
4-(3-(4-methoxyphenyl)oxetan-3-yl)-2-methylphenyl trifluoromethanesulfonate [ No CAS ]
4-(4-(3-(4-methoxyphenyl)oxetan-3-yl)-2-methylphenyl)-3-(trifluoromethyl)-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 130℃; for 14h; Cooling; Inert atmosphere;

Reference： [1]Bull, James A.; Choi, Chulho; Croft, Rosemary A.; Ding, Yujie; Dubois, Maryne A. J.; Mousseau, James J.; Owen, Dafydd R. [2021, vol. 12, # 12, p. 2045 - 2052]

22
[ 1218790-40-9 ]
4-(4-methoxybenzoyl)-2-methylphenyl trifluoromethanesulfonate [ No CAS ]
(4-methoxyphenyl)(3-methyl-4-(3-(trifluoromethyl)-1H-pyrazol-4-yl)phenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 130℃; for 14h; Cooling; Inert atmosphere;

Reference： [1]Bull, James A.; Choi, Chulho; Croft, Rosemary A.; Ding, Yujie; Dubois, Maryne A. J.; Mousseau, James J.; Owen, Dafydd R. [2021, vol. 12, # 12, p. 2045 - 2052]

23
[ 1218790-40-9 ]
tert-butyl 4-[(5-bromo-1-methylimidazole-2-carbonyl)amino]-2-chlorobenzoate [ No CAS ]
tert-butyl 2-chloro-4-(1-methyl-5-(3-(trifluoromethyl)-1H-pyrazol-4-yl)-1H-imidazole-2-carboxamido)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2 g	With dichloro[ 1,1’-bis(di-tert-butylphosphino)ferrocene]palladium (II); anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate for 15h; Inert atmosphere;	tert-Butyl 2-chloro-4-[[l-methyl-5-[3-(trifluoromethyl)-lH-pyrazol-4-yl]imidazole-2- carbonyl] amino] benzoate In a 100 mL round-bottomed flask, tert-butyl 4-(5-bromo-l-methyl-imidazole-2-carboxamido)- 2-chlorobenzoate (2 g, 4.82 mmol), 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3- (trifluoromethyl)-lH-pyrazole (1.64 g, 6.27 mmol), l,l'-bis(di-tert-butylphosphino)ferrocene palladium dichloride (314 mg, 482 pmol) and Na2CO3 (1.53 g, 14.5 mmol) were combined with 1,4-Dioxane (30 mL)Water (3 mL) and stirred for 15 h under N2. The filtrate was concentrated in vacuum. The crude material was purified by flash chromatography (silica gel, 20 g, 0 % to 10 % MeOH in DCM) to afford tert-butyl 2-chloro-4-(l-methyl-5-(3-(trifluoromethyl)- lH-pyrazol-4-yl)-imidazole-2-carboxamido)benzoate (2 g). MS [M+H]+: 470.7.
2 g	With dichloro[ 1,1’-bis(di-tert-butylphosphino)ferrocene]palladium (II); anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate for 15h; Inert atmosphere;	tert-Butyl 2-chloro-4-[[l-methyl-5-[3-(trifluoromethyl)-lH-pyrazol-4-yl]imidazole-2- carbonyl] amino] benzoate In a 100 mL round-bottomed flask, tert-butyl 4-(5-bromo-l-methyl-imidazole-2-carboxamido)- 2-chlorobenzoate (2 g, 4.82 mmol), 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3- (trifluoromethyl)-lH-pyrazole (1.64 g, 6.27 mmol), l,l'-bis(di-tert-butylphosphino)ferrocene palladium dichloride (314 mg, 482 pmol) and Na2CO3 (1.53 g, 14.5 mmol) were combined with 1,4-Dioxane (30 mL)Water (3 mL) and stirred for 15 h under N2. The filtrate was concentrated in vacuum. The crude material was purified by flash chromatography (silica gel, 20 g, 0 % to 10 % MeOH in DCM) to afford tert-butyl 2-chloro-4-(l-methyl-5-(3-(trifluoromethyl)- lH-pyrazol-4-yl)-imidazole-2-carboxamido)benzoate (2 g). MS [M+H]+: 470.7.
2 g	With dichloro[ 1,1’-bis(di-tert-butylphosphino)ferrocene]palladium (II); anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 100℃; for 15h; Inert atmosphere;	tert-Butyl 2-chloro-4-[[1-methyl-5-[3-(trifluoromethyl)-1H-pyrazol-4-yl]imidazole-2- carbonyl] amino] benzoate In a 100 mL round-bottomed flask, tert-butyl 4-(5-bromo-1-methyl-imidazole-2-carboxamido)- 2-chlorobenzoate (2 g, 4.82 mmol) , 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3- (trifluoromethyl)- 1 H-pyrazole (1.64 g, 6.27 mmol), 1,1'-bis(di-tert-butylphosphino)ferrocene palladium dichloride (314 mg, 482 μmol) and Na2CO3 (1.53 g, 14.5 mmol) were combined with 1,4-Dioxane (30 mL) Water (3 mL) and stirred at 100 °C for 15 h under N2. The filtrate was concentrated in vacuum. The crude material was purified by flash chromatography (silica gel , 20 g , 0 % to 10 % MeOH in DCM ) to afford tert-butyl 2-chloro-4-(1-methyl-5-(3- (trifluoromethyl)-1H-pyrazol-4-yl)-imidazole-2-carboxamido)benzoate (2 g) . MS [M+H]+ : 470.7.

2 g	With dichloro[ 1,1’-bis(di-tert-butylphosphino)ferrocene]palladium (II); anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 100℃; for 15h; Inert atmosphere;	tert-Butyl 2-chloro-4-[[1-methyl-5-[3-(trifluoromethyl)-1H-pyrazol-4-yl]imidazole-2- carbonyl] amino] benzoate In a 100 mL round-bottomed flask, tert-butyl 4-(5-bromo-1-methyl-imidazole-2-carboxamido)- 2-chlorobenzoate (2 g, 4.82 mmol) , 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3- (trifluoromethyl)- 1 H-pyrazole (1.64 g, 6.27 mmol), 1,1'-bis(di-tert-butylphosphino)ferrocene palladium dichloride (314 mg, 482 μmol) and Na2CO3 (1.53 g, 14.5 mmol) were combined with 1,4-Dioxane (30 mL) Water (3 mL) and stirred at 100 °C for 15 h under N2. The filtrate was concentrated in vacuum. The crude material was purified by flash chromatography (silica gel , 20 g , 0 % to 10 % MeOH in DCM ) to afford tert-butyl 2-chloro-4-(1-methyl-5-(3- (trifluoromethyl)-1H-pyrazol-4-yl)-imidazole-2-carboxamido)benzoate (2 g) . MS [M+H]+ : 470.7.
2 g	With dichloro[ 1,1’-bis(di-tert-butylphosphino)ferrocene]palladium (II); anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 100℃; for 15h; Inert atmosphere;	tert-Butyl 2-chloro-4-[[1-methyl-5-[3-(trifluoromethyl)-1H-pyrazol-4-yl]imidazole-2- carbonyl] amino] benzoate In a 100 mL round-bottomed flask, tert-butyl 4-(5-bromo-1-methyl-imidazole-2-carboxamido)- 2-chlorobenzoate (2 g, 4.82 mmol) , 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3- (trifluoromethyl)- 1 H-pyrazole (1.64 g, 6.27 mmol), 1,1'-bis(di-tert-butylphosphino)ferrocene palladium dichloride (314 mg, 482 μmol) and Na2CO3 (1.53 g, 14.5 mmol) were combined with 1,4-Dioxane (30 mL) Water (3 mL) and stirred at 100 °C for 15 h under N2. The filtrate was concentrated in vacuum. The crude material was purified by flash chromatography (silica gel , 20 g , 0 % to 10 % MeOH in DCM ) to afford tert-butyl 2-chloro-4-(1-methyl-5-(3- (trifluoromethyl)-1H-pyrazol-4-yl)-imidazole-2-carboxamido)benzoate (2 g) . MS [M+H]+ : 470.7.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2022/49011, 2022, A1 Location in patent: Page/Page column 84
[2]Current Patent Assignee: ROCHE HOLDING AG - WO2022/49011, 2022, A1 Location in patent: Page/Page column 84
[3]Current Patent Assignee: ROCHE HOLDING AG - WO2022/43486, 2022, A1 Location in patent: Page/Page column 73
[4]Current Patent Assignee: ROCHE HOLDING AG - WO2022/43486, 2022, A1 Location in patent: Page/Page column 73
[5]Current Patent Assignee: ROCHE HOLDING AG - WO2022/43486, 2022, A1 Location in patent: Page/Page column 51; 73

24
[ 4548-45-2 ]
[ 1218790-40-9 ]
5-nitro-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyrazol-1-yl]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10 g	With triethylamine In dimethyl sulfoxide at 130℃; for 3h; Inert atmosphere;	5-Nitro-2-[4-(4,4,5,5-tetramethyI-l,3,2-dioxaborolan-2-yI)-3-(trifluoromethyI)pyrazol-l- yl] pyridine To a solution of 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-lH-pyrazole (7.8 g, 30 mmol) in dimethy sulfoxide (100 mL) and triethyl amine (3.0 mL) was added 2- chl oro-5 -nitro-pyridine (4.8 g, 30 mmol). Then the mixture was stirred for 3 h at 130 °C. The mixture was poured into water and the aqueous solution was extracted with DCM. The combined organic layers were washed with water and brine, dried over anhydrous Na2SO4. The organic layer was concentrated in vacuum and the residue was purified by flash column to afford 5-nitro- 2-[4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyrazol-l-yl]pyridine (10 g) as a yellow solid. MS [M+H]+: 385.1.
10 g	With triethylamine In dimethyl sulfoxide at 130℃; for 3h; Inert atmosphere;	5-Nitro-2-[4-(4,4,5,5-tetramethyI-l,3,2-dioxaborolan-2-yI)-3-(trifluoromethyI)pyrazol-l- yl] pyridine To a solution of 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-lH-pyrazole (7.8 g, 30 mmol) in dimethy sulfoxide (100 mL) and triethyl amine (3.0 mL) was added 2- chl oro-5 -nitro-pyridine (4.8 g, 30 mmol). Then the mixture was stirred for 3 h at 130 °C. The mixture was poured into water and the aqueous solution was extracted with DCM. The combined organic layers were washed with water and brine, dried over anhydrous Na2SO4. The organic layer was concentrated in vacuum and the residue was purified by flash column to afford 5-nitro- 2-[4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyrazol-l-yl]pyridine (10 g) as a yellow solid. MS [M+H]+: 385.1.
10 g	With triethylamine In dimethyl sulfoxide at 130℃; for 3h;	5-Nitro-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyrazol-1- yl] pyridine To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole (7.8 g, 30 mmol) in dimethy sulfoxide (100 ml) and triethyl amine (3.0 ml) was added 2-chloro- 5-nitro-pyridine (4.8 g, 30 mmol). Then the mixture was stirred for 3 h at 130 °C. The mixture was poured into water and the aqueous solution was extracted with DCM. The combined organic layers were washed with water and brine, dried over anhydrous Na2S04. The organic layer was concentrated in vacuum and the residue was purified by flash column to afford 5-nitro-2-[4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyrazol-1-yl]pyridine (10 g) as a yellow solid. MS [M+H]+: 385.1.

10 g	With triethylamine In dimethyl sulfoxide at 130℃; for 3h;	5-Nitro-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyrazol-1- yl] pyridine To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole (7.8 g, 30 mmol) in dimethy sulfoxide (100 ml) and triethyl amine (3.0 ml) was added 2-chloro- 5-nitro-pyridine (4.8 g, 30 mmol). Then the mixture was stirred for 3 h at 130 °C. The mixture was poured into water and the aqueous solution was extracted with DCM. The combined organic layers were washed with water and brine, dried over anhydrous Na2S04. The organic layer was concentrated in vacuum and the residue was purified by flash column to afford 5-nitro-2-[4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyrazol-1-yl]pyridine (10 g) as a yellow solid. MS [M+H]+: 385.1.
10 g	With triethylamine In dimethyl sulfoxide at 130℃; for 3h; Inert atmosphere;	5-Nitro-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyrazol-1- yl] pyridine To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole (7.8 g, 30 mmol) in dimethy sulfoxide (100 ml) and triethyl amine (3.0 ml) was added 2-chloro- 5-nitro-pyridine (4.8 g, 30 mmol). Then the mixture was stirred for 3 h at 130 °C. The mixture was poured into water and the aqueous solution was extracted with DCM. The combined organic layers were washed with water and brine, dried over anhydrous Na2S04. The organic layer was concentrated in vacuum and the residue was purified by flash column to afford 5-nitro-2-[4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyrazol-1-yl]pyridine (10 g) as a yellow solid. MS [M+H]+: 385.1.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - WO2022/49011, 2022, A1 Location in patent: Page/Page column 60; 77-78
[2]Current Patent Assignee: ROCHE HOLDING AG - WO2022/49011, 2022, A1 Location in patent: Page/Page column 60; 77-78
[3]Current Patent Assignee: ROCHE HOLDING AG - WO2022/43486, 2022, A1 Location in patent: Page/Page column 53
[4]Current Patent Assignee: ROCHE HOLDING AG - WO2022/43486, 2022, A1 Location in patent: Page/Page column 53
[5]Current Patent Assignee: ROCHE HOLDING AG - WO2022/43486, 2022, A1 Location in patent: Page/Page column 51; 53

25
[ 2969-81-5 ]
[ 1218790-40-9 ]
ethyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)butanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium carbonate In N,N-dimethyl-formamide at 180℃; for 16h;

Reference： [1]Che, Jianwei; Gray, Nathanael S.; Hatcher, John M.; Jiang, Jie; Powell, Chelsea E.; Vatsan, Prasanna S. [ACS Medicinal Chemistry Letters, 2022, vol. 13, # 4, p. 577 - 585]

26
[ 1218790-40-9 ]
[ 110661-91-1 ]
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)butanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium carbonate In N,N-dimethyl-formamide at 180℃; for 16h;

Reference： [1]Che, Jianwei; Gray, Nathanael S.; Hatcher, John M.; Jiang, Jie; Powell, Chelsea E.; Vatsan, Prasanna S. [ACS Medicinal Chemistry Letters, 2022, vol. 13, # 4, p. 577 - 585]

27
[ 1218790-40-9 ]
C₁₁H₇BrFN₃OS [ No CAS ]
C₁₅H₉F₄N₅OS [ No CAS ]
C₁₅H₉F₄N₅OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; potassium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 80℃; for 8h; Inert atmosphere;	2 ntermediate B (124 mg, 378 μmol) and compound 2-1 (99 mg, 378 μmol) were dissolved in 1,4-dioxane (4 mL) and water (1 mL), and potassium carbonate (157 mg, 157 mg, 1 mL) was added to the reaction solution. 1.13 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (28 mg, 38 μmol). The reaction solution was heated to 80°C under nitrogen protection for 8 hours. The reaction solution was concentrated under reduced pressure, and the crude product was separated by silica gel column chromatography (petroleum ether/ethyl acetate, 3/11/1, V/V) to obtain a crude mixture of 2a and 2b. The crude product was subjected to SFC (separating column: DAICEL). CHIRALPAK AD 250mm×30mm×10μm; mobile phase: supercritical CO 2-0.1% ammonia solution in ethanol; gradient: 0.1% ammonia solution in ethanol 35%-35%) to separate compounds 2a (the first peak) and 2b ( the second peak). The two compounds were then analyzed by SFC (column: Chiralcel AD-3 50mm×4.6mm×3μm; mobile phase: supercritical CO 2-0.05% diethylamine in ethanol; gradient: 0.05% diethylamine in ethanol: 5 %-40%) measured e.e. value.

Reference： [1]Current Patent Assignee: WUXI APPTEC CO., LTD. - WO2022/143693, 2022, A1 Location in patent: Page/Page column 21-22

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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
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. 1218790-40-9 ] {[proInfo.proName]}

Quality Control of [ 1218790-40-9 ]

Related Doc. of [ 1218790-40-9 ]

Product Details of [ 1218790-40-9 ]

Safety of [ 1218790-40-9 ]

Application In Synthesis of [ 1218790-40-9 ]

[ 1218790-40-9 ] Synthesis Path-Downstream 1~27

Related Functional Groups of [ 1218790-40-9 ]

Fluorinated Building Blocks

Organoboron

Esters

Trifluoromethyls

Related Parent Nucleus of [ 1218790-40-9 ]

Pyrazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1218790-40-9 ]

Related Parent Nucleus of
[ 1218790-40-9 ]