[ CAS No. 89607-15-8 ] {[proInfo.proName]}

Name: 89607-15-8|3-Bromo-1-methyl-4-nitro-1H-pyrazole|97%
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Quality Control of [ 89607-15-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 89607-15-8 ]

CAS No. :	89607-15-8	MDL No. :	MFCD00466335
Formula :	C₄H₄BrN₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BHFRSRAZJCLLDY-UHFFFAOYSA-N
M.W :	206.00	Pubchem ID :	13185127
Synonyms :

Calculated chemistry of [ 89607-15-8 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.25
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	40.01
TPSA :	63.64 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.78 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.3
Log Po/w (XLOGP3) :	1.09
Log Po/w (WLOGP) :	1.09
Log Po/w (MLOGP) :	0.52
Log Po/w (SILICOS-IT) :	-0.94
Consensus Log Po/w :	0.61

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.11
Solubility :	1.61 mg/ml ; 0.0078 mol/l
Class :	Soluble
Log S (Ali) :	-2.02
Solubility :	1.97 mg/ml ; 0.00958 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.04
Solubility :	19.0 mg/ml ; 0.092 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.03

Safety of [ 89607-15-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 89607-15-8 ]

* 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.

Upstream synthesis route of [ 89607-15-8 ]
Downstream synthetic route of [ 89607-15-8 ]

[ 89607-15-8 ] Synthesis Path-Upstream 1~5

1
[ 77-78-1 ]
[ 155600-99-0 ]
[ 89607-15-8 ]
[ 89607-13-6 ]
[ 3994-50-1 ]

Reference： [1] Russian Chemical Bulletin, 2012, vol. 61, # 1, p. 209 - 210[2] Izv. Akad. Nauk, Ser. Khim., 2012, # 1, p. 206 - 207

2
[ 20055-00-9 ]
[ 89607-15-8 ]

Reference： [1] Patent: WO2016/144848, 2016, A1, . Location in patent: Page/Page column 38
[2] Patent: WO2016/144846, 2016, A1, . Location in patent: Page/Page column 53; 54
[3] Patent: WO2016/144849, 2016, A1, . Location in patent: Page/Page column 33
[4] Patent: WO2016/144847, 2016, A1, . Location in patent: Page/Page column 36; 37

3
[ 77-78-1 ]
[ 155600-99-0 ]
[ 89607-15-8 ]
[ 89607-13-6 ]
[ 3994-50-1 ]

Reference： [1] Russian Chemical Bulletin, 2012, vol. 61, # 1, p. 209 - 210[2] Izv. Akad. Nauk, Ser. Khim., 2012, # 1, p. 206 - 207

4
[ 77-78-1 ]
[ 155600-99-0 ]
[ 89607-15-8 ]
[ 89607-13-6 ]
[ 3994-50-1 ]

Reference： [1] Russian Chemical Bulletin, 2012, vol. 61, # 1, p. 209 - 210[2] Izv. Akad. Nauk, Ser. Khim., 2012, # 1, p. 206 - 207

5
[ 77-78-1 ]
[ 155600-99-0 ]
[ 89607-15-8 ]
[ 89607-13-6 ]
[ 3994-50-1 ]

Reference： [1] Russian Chemical Bulletin, 2012, vol. 61, # 1, p. 209 - 210[2] Izv. Akad. Nauk, Ser. Khim., 2012, # 1, p. 206 - 207

[ 89607-15-8 ] Synthesis Path-Downstream 1~9

1
1-bromo-4-nitropyrazole [ No CAS ]
[ 77-78-1 ]
[ 155600-99-0 ]
[ 89607-15-8 ]
[ 89607-13-6 ]
[ 3994-50-1 ]

Reference： [1]Russian Chemical Bulletin,2012,vol. 61,p. 209 - 210
Izv. Akad. Nauk, Ser. Khim.,2012,p. 206 - 207

2
[ 20055-00-9 ]
[ 89607-15-8 ]

Yield	Reaction Conditions	Operation in experiment
	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 0 - 25℃; for 2h;	Step 4: Into a 250 mL round bottom flask containing a solution of copper(II) bromide (3.0 g, 14 mmol) and tert-butyl nitrite (1.7 mL, 14 mmol) in acetonitrile (150 mL) was added 1-methyl-4- nitro-1H-pyrazol-3-amine (2 g, 14 mmol) in acetonitrile (20 mL) at 0 C and the reaction was stirred at room temperature for 2 h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (120 mL), washed with water and brine,dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Theresidue was purified by column chromatography eluting with ethyl acetate in petroleum ether(20-30%) to afford 3-bromo-1-methyl-4-nitro-1H-pyrazole as a solid. ?H NMR (CDC13, 300MHz): 5 8.25 (s, 1H), 3.89 (s, 3H).
	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 0 - 25℃; for 2.08333h;	Step 3: A mixture of copper(II) bromide (5.5 g, 25 mmol) and tert-butyl nitrite (2.5 g, 25 mmol) in acetonitrile (100 mL) was taken into a 250 mL round bottom flask and cooled to 0 C. Asolution of 1-methyl-4-nitro-1H-pyrazol-3-amine (3.5 g, 25 mmol) in acetonitrile (20 mL) was added dropwise over a period of 5 mm. The reaction mixture was slowly warmed to room temperature and stirred for 2 h. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with ethyl acetate in petroleum ether (15-20%) to afford 3-bromo-1-methyl-4-nitro-1H-pyrazole as a solid. ?H NMR (DM50-cl6, 400 MHz): 8.94 (s, 1H), 3.89 (s, 3H).
	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 0 - 20℃; for 2h;	Stpe 4: Into a 250 mL round bottom flask containing a solution of copper(II) bromide (3.0 g, 14 mmol) and fert-butyl nitrite (1.7 mL, 14 mmol) in acetonitrile (150 mL) was added l-methyl-4- nitro-lH-pyrazol-3-amine (2 g, 14 mmol) in acetonitrile (20 mL) at 0 C and the reaction was stirred at room temperature for 2 h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (120 mL), washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography eluting with ethyl acetate in petroleum ether (20-30%) to afford 3-bromo-l-methyl-4-nitro-lH-pyrazole as a solid. NMR (CDC13, 300 MHz): delta 8.25 (s, 1H), 3.89 (s, 3H).

With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 0 - 20℃; for 2h;

Step 4: Into a 250 mL round bottom flask containing a solution of copper(II) bromide (3.0 g, 14 mmol) and tert-butyl nitrite (1.7 mL, 14 mmol) in acetonitrile (150 mL) was added 1-methyl-4- nitro-1H-pyrazol-3-amine (2 g, 14 mmol) in acetonitrile (20 mL) at 0 oC and the reaction was stirred at room temperature for 2 h. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (120 mL), washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography eluting with ethyl acetate in petroleum ether (20-30%) to afford 3-bromo-1-methyl-4-nitro-1H-pyrazole as a solid. 1H NMR (CDCl3, 300 MHz): delta 8.25 (s, 1H), 3.89 (s, 3H).

Reference： [1]Patent: WO2016/144848,2016,A1 .Location in patent: Page/Page column 38
[2]Patent: WO2016/144846,2016,A1 .Location in patent: Page/Page column 53; 54
[3]Patent: WO2016/144849,2016,A1 .Location in patent: Page/Page column 33
[4]Patent: WO2016/144847,2016,A1 .Location in patent: Page/Page column 36; 37

3
[ 89607-15-8 ]
3-bromo-1-methyl-1H-pyrazol-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; In ethyl acetate; at 25℃; for 16h;	Step 5: Into a 100 mL round bottom flask containing a solution of <strong>[89607-15-8]3-bromo-1-methyl-4-nitro-1H-pyrazole</strong> (1.0 g) in ethyl acetate (50 mL) at room temperature was added Raney Nickel (700mg) and the reaction mixture was stirred at room temperature for 16 h under hydrogen atmosphere. The reaction mixture was filtered through celite and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and purified by flash chromatography eluting with ethyl acetate in petroleum ether (40-50%) to afford 3-bromo-1-methyl-1H-pyrazol- 4-amine as a liquid. ?H NMR (CD3OD, 400 MHz): 5 7.18 (s, 1H), 3.77 (s, 3H). MS calc?d [M+Hj 176.0, found 176.2.
	With hydrogen; In ethyl acetate; at 25℃; for 16h;	Step 5: Into a 100 mL round bottom flask containing a solution of <strong>[89607-15-8]3-bromo-1-methyl-4-nitro-1H-pyrazole</strong> (1.0 g) in ethyl acetate (50 mL) at room temperature was added Raney Nickel (700mg) and the reaction mixture was stirred at room temperature for 16 h under hydrogen atmosphere. The reaction mixture was filtered through celite and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and purified by flash chromatography eluting with ethyl acetate in petroleum ether (40-50%) to afford 3-bromo-1-methyl-1H-pyrazol- 4-amine as a liquid. ?H NMR (CD3OD, 400 MHz): 7.18 (s, 1H), 3.77 (s, 3H). MS calc?d[M+Hj 176.0, found 176.2.
	With hydrogen; In ethyl acetate; at 20℃; for 16h;	Stpe 5: Into a 100 mL round bottom flask containing a solution of 3-bromo-l-methyl-4-nitro- lH-pyrazole (1.0 g) in ethyl acetate (50 mL) at room temperature was added Raney Nickel (700 mg) and the reaction mixture was stirred at room temperature for 16 h under hydrogen atmosphere. The reaction mixture was filtered through celite and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and purified by flash chromatography eluting with ethyl acetate in petroleum ether (40-50%) to afford 3-bromo-l -methyl- lH-pyrazol- 4-amine as a liquid. 1 NMR (CD3OD, 400 MHz): delta 7.18 (s, 1H), 3.77 (s, 3H). MS calc'd [M+H]+ 176.0, found 176.2.

With hydrogen; In ethyl acetate; at 20℃; for 16h;

Step 5: Into a 100 mL round bottom flask containing a solution of 3-bromo-1-methyl-4-nitro- 1H-pyrazole (1.0 g) in ethyl acetate (50 mL) at room temperature was added Raney Nickel (700 mg) and the reaction mixture was stirred at room temperature for 16 h under hydrogen atmosphere. The reaction mixture was filtered through celite and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and purified by flash chromatography eluting with ethyl acetate in petroleum ether (40-50%) to afford 3-bromo-1-methyl-1H-pyrazol-4-amine as a liquid. 1H NMR (CD3OD, 400 MHz): delta 7.18 (s, 1H), 3.77 (s, 3H). MS calc?d [M+H]+ 176.0, found 176.2

Reference： [1]Patent: WO2016/144848,2016,A1 .Location in patent: Page/Page column 37; 38; 39
[2]Patent: WO2016/144846,2016,A1 .Location in patent: Page/Page column 56; 57
[3]Patent: WO2016/144849,2016,A1 .Location in patent: Page/Page column 33
[4]Patent: WO2016/144847,2016,A1 .Location in patent: Page/Page column 37

4
[ 7486-35-3 ]
[ 89607-15-8 ]
1-methyl-4-nitro-3-vinyl-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); In toluene; at 120℃; for 6h;	Step 4: Into a 25 mL round bottom flask containing a solution of 3-bromo-1-methyl-4-nitro-1H- pyrazole (1.0 g, 5 mmol) in toluene (5 mL) were added tributyl(vinyl)tin (1.7 mL, 58 mmol) andtetrakis(triphenylphosphine)palladium(0) (300 mg, 0.25 mmol) and the reaction was heated at120 C for 6 h. The reaction mixture was cooled to room temperature, concentrated and purifiedby flash chromatography eluting with ethyl acetate in petroleum ether (15-20%) to afford 1-methyl-4-nitro-3-vinyl-1H-pyrazole as a solid. ?H NMR (CDC13, 300 MHz): 8.07 (s, 1H), 7.22(dd,J= 17.6, 11.2 Hz, 1H), 6.19 (dd,J= 17.7, 4.6 Hz, 1H), 5.54(dd,J= 11.1, 1.6 Hz, 1H), 3.97(s, 3H).

Reference： [1]Patent: WO2016/144846,2016,A1 .Location in patent: Page/Page column 54

5
[ 89607-15-8 ]
[ 1692-15-5 ]
4-(1-methyl-4-nitro-1H-pyrazol-3-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 80℃; for 14h;Sealed tube; Inert atmosphere;	Step 1: Into a 10 mL sealed tube containing a solution of 3-bromo-1-methyl-4-nitro-JH-pyrazole (800 mg, 0.4 mmol) in 1,4-dioxane (2 mL) were added potassium phosphate tribasic (140 mg,0.7 mmol) in water (1 mL) and pyridin-4-ylboronic acid (70 mg, 0.6 mmol) and the mixture was degassed with nitrogen for 10 mm. [1,1?-bis(diphenylphosphino)ferrocenej dichloropalladium(II),complex with dichloromethane (20 mg, 0.03 mmol) was added and the reaction mixture was heated at 80 C for 14 h. The reaction mixture was filtered thorugh celite and the filterate was concentrated under reduced pressure.The residue was purified by flash chromatography eluting with ethyl acetate in petroleum ether (10-15%) to yield 4-(1-methyl-4-nitro-1H-pyrazol-3-yl)pyridine. ?H NMR (DMSO-d6, 300 MHz): oe 8.98 (s, 1H), 8.67 (d, J 6.1 Hz, 2H), 7.62 (d, J 6.1 Hz, 2H), 3.95 (s, 3H). MS calc?d [M+Hj 205.1, found 205.2.

Reference： [1]Patent: WO2016/144846,2016,A1 .Location in patent: Page/Page column 59

6
[ 784193-37-9 ]
[ 74-88-4 ]
[ 89607-15-8 ]

Yield	Reaction Conditions	Operation in experiment
58%	With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 25℃; for 2h;	To a mixture of 3-bromo-4-nitro-1H-pyrazole (6.20 g, 32.3 mmol) and K2CO3 (5.36 g, 38.7 mmol) in DMF (40 mL) was added MeI (5.50 g, 38.7 mmol) at 0 C. Then, the mixture was stirred at 25 C. for 2 hours. On completion, the mixture was diluted with water (200 mL), then extracted with EA (3×80 mL). The combined organic layer was washed with brine (50 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography over silica gel (PE:EA=20:1-3:1) to give the title compound (3.90 g, 58% yield) as light yellow solid. 1H NMR (400 MHz, CDCl3) delta 8.16 (s, 1H), 3.97 (s, 3H).

Reference： [1]Patent: US2019/192668,2019,A1 .Location in patent: Paragraph 4073; 4075

7
[ 89607-15-8 ]
methyl 5-(1-methyl-4-nitropyrazol-3-yl)pyridine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydrogencarbonate; In 1,4-dioxane; dichloromethane; water; at 80℃; for 2h;Inert atmosphere;	A mixture of 3-bromo-1-methyl-4-nitro-pyrazole (3.80 g, 18.4 mmol), (5-methoxycarbonyl-3-pyridyl)boronic acid (4.67 g, 25.8 mmol, CAS871329-53-2), Pd(dppf)Cl2.CH2Cl2 (800 mg, 979 umol) and NaHCO3 (3.10 g, 36.8 mmol) in dioxane (50 mL) and H2O (10 mL) was stirred at 80 C. under N2 for 2 hours. On completion, the mixture was cooled to 25 C. The mixture was diluted with water (100 mL), then extracted with EA (3×80 mL). The combined organic layer was washed with brine (50 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (PE:EA=5:1-DCM:EA=2:1) to give the title compound (2.95 g, 61% yield) as light yellow solid. 1H NMR (400 MHz, CDCl3) delta 9.29 (s, 1H), 9.12 (s, 1H), 8.68 (s, 1H), 8.31 (s, 1H), 4.05 (s, 3H), 4.00 (s, 3H).

Reference： [1]Patent: US2019/192668,2019,A1 .Location in patent: Paragraph 4073; 4076

8
[ 959996-48-6 ]
[ 89607-15-8 ]
3-(2-bromo-5-fluorophenyl)-1-methyl-4-nitropyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate In 1,4-dioxane; water at 110℃; Inert atmosphere;	26.26-1 Example 26-1 : Synthesis of 3-(2-bromo-5-fluorophenyl)-1-methyl-4- nitropyrazole To a stirred mixture of 2-bromo-5-fluorophenylboronic acid (700 mg, 3.039 mmol) and 3-bromo-1 -methyl-4-nitropyrazole (700 mg, 3.330 mmol) in dioxane (28 mL) and H2O (7 mL) were added NaHCCb (1.40 g, 15.832 mmol) and Pd(PPh3)4 (350 mg, 0.300 mmol). The resulting mixture was stirred overnight at 110°C under nitrogen atmosphere and then concentrated under vacuum. The residue was extracted with EtOAc (3 x 30mL) and the combined organic layers were washed with brine (1x50 mL) and dried over anhydrous Na2S04. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with PE/EtOAc (4:1 ) to afford 3-(2-bromo-5-fluorophenyl)-1-methyl-4-nitropyrazole (700 mg, 40%) as a white solid.
40%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate In 1,4-dioxane; water at 110℃; Inert atmosphere;	26.26-1 Example 26-1 : Synthesis of 3-(2-bromo-5-fluorophenyl)-1-methyl-4- nitropyrazole To a stirred mixture of 2-bromo-5-fluorophenylboronic acid (700 mg, 3.039 mmol) and 3-bromo-1 -methyl-4-nitropyrazole (700 mg, 3.330 mmol) in dioxane (28 mL) and H2O (7 mL) were added NaHCCb (1.40 g, 15.832 mmol) and Pd(PPh3)4 (350 mg, 0.300 mmol). The resulting mixture was stirred overnight at 110°C under nitrogen atmosphere and then concentrated under vacuum. The residue was extracted with EtOAc (3 x 30mL) and the combined organic layers were washed with brine (1x50 mL) and dried over anhydrous Na2S04. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with PE/EtOAc (4:1 ) to afford 3-(2-bromo-5-fluorophenyl)-1-methyl-4-nitropyrazole (700 mg, 40%) as a white solid.

Reference： [1]Current Patent Assignee: MERCK KGAA; CANCER RESEARCH UK - WO2021/224291, 2021, A1 Location in patent: Page/Page column 187
[2]Current Patent Assignee: MERCK KGAA; CANCER RESEARCH UK - WO2021/224291, 2021, A1 Location in patent: Page/Page column 187

9
[ 913835-93-5 ]
[ 89607-15-8 ]
ethyl 3-(4-amino-1-methyl-1H-pyrazol-3-yl)-4-chlorobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 90℃; for 16h; Inert atmosphere;	4.4-1 Example 4-1 : Synthesis of ethyl 3-(4-amino-1 -methyl-1 H-pyrazol-3-yl)-4- chlorobenzoate The mixture of 2-chloro-5-(ethoxycarbonyl)phenyl]boronic acid (1.20 g; 5.20 mmol), 3-bromo-1 -methyl-1 H-pyrazol-4-amine (915 mg; 5.20 mmol), CS2CO3(3.4 g; 10.40 mmol) and Pd(dppf)Cl2 (380 mg; 0.52 mmol) in dioxane (20 ml) and water (2 ml) was stirred under N2 atmosphere at 90°C for 16h. The mixture was filtered and concentrated to get crude product as a black oil. The crude was purified by C18 (ACN/H20 = 20% - 95%) to get the product. (355 mg; 23 %; light brown oil).1H NMR (400 MHz, DMSO) δ 7.97 (d, J = 2.2 Hz, 1 H), 7.92 C 7.87 (m, 1 H),7.67 (d, J = 8.4 Hz, 1 H), 7.17 (s, 1 H), 4.32 (d, J = 7.1 Hz, 2H), 3.76 (s, 3H), 1.32 (t, J = 7.1 Hz, 3H).
23%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 90℃; for 16h; Inert atmosphere;	4.4-1 Example 4-1 : Synthesis of ethyl 3-(4-amino-1 -methyl-1 H-pyrazol-3-yl)-4- chlorobenzoate The mixture of 2-chloro-5-(ethoxycarbonyl)phenyl]boronic acid (1.20 g; 5.20 mmol), 3-bromo-1 -methyl-1 H-pyrazol-4-amine (915 mg; 5.20 mmol), CS2CO3(3.4 g; 10.40 mmol) and Pd(dppf)Cl2 (380 mg; 0.52 mmol) in dioxane (20 ml) and water (2 ml) was stirred under N2 atmosphere at 90°C for 16h. The mixture was filtered and concentrated to get crude product as a black oil. The crude was purified by C18 (ACN/H20 = 20% - 95%) to get the product. (355 mg; 23 %; light brown oil).1H NMR (400 MHz, DMSO) δ 7.97 (d, J = 2.2 Hz, 1 H), 7.92 C 7.87 (m, 1 H),7.67 (d, J = 8.4 Hz, 1 H), 7.17 (s, 1 H), 4.32 (d, J = 7.1 Hz, 2H), 3.76 (s, 3H), 1.32 (t, J = 7.1 Hz, 3H).

Reference： [1]Current Patent Assignee: MERCK KGAA; CANCER RESEARCH UK - WO2021/224291, 2021, A1 Location in patent: Page/Page column 155
[2]Current Patent Assignee: MERCK KGAA; CANCER RESEARCH UK - WO2021/224291, 2021, A1 Location in patent: Page/Page column 155

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P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
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. 89607-15-8 ] {[proInfo.proName]}

Quality Control of [ 89607-15-8 ]

Related Doc. of [ 89607-15-8 ]

Product Details of [ 89607-15-8 ]

Calculated chemistry of [ 89607-15-8 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 89607-15-8 ]

Application In Synthesis of [ 89607-15-8 ]

[ 89607-15-8 ] Synthesis Path-Upstream 1~5

[ 89607-15-8 ] Synthesis Path-Downstream 1~9

Related Functional Groups of [ 89607-15-8 ]

Bromides

Nitroes

Related Parent Nucleus of [ 89607-15-8 ]

Pyrazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 89607-15-8 ]

Related Parent Nucleus of
[ 89607-15-8 ]