[ CAS No. 73387-52-7 ] {[proInfo.proName]}

Name: 73387-52-7|5-(4-Bromophenyl)-1-methyl-1H-pyrazole|98%
Brand: Ambeed
SKU: A131171
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Quality Control of [ 73387-52-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 73387-52-7 ]

SDS Specification

Alternatived Products of [ 73387-52-7 ]

Product Details of [ 73387-52-7 ]

CAS No. :	73387-52-7	MDL No. :	MFCD10699189
Formula :	C₁₀H₉BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CVCDEENQBMSJCX-UHFFFAOYSA-N
M.W :	237.10	Pubchem ID :	12581092
Synonyms :

Calculated chemistry of [ 73387-52-7 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.1
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	56.63
TPSA :	17.82 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.91 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.33
Log Po/w (XLOGP3) :	2.59
Log Po/w (WLOGP) :	2.85
Log Po/w (MLOGP) :	2.47
Log Po/w (SILICOS-IT) :	2.65
Consensus Log Po/w :	2.58

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.5
Solubility :	0.0747 mg/ml ; 0.000315 mol/l
Class :	Soluble
Log S (Ali) :	-2.61
Solubility :	0.578 mg/ml ; 0.00244 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.17
Solubility :	0.0159 mg/ml ; 0.0000671 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.7

Safety of [ 73387-52-7 ]

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 [ 73387-52-7 ]

* 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 [ 73387-52-7 ]
Downstream synthetic route of [ 73387-52-7 ]

[ 73387-52-7 ] Synthesis Path-Upstream 1~6

1
[ 73387-46-9 ]
[ 74-88-4 ]
[ 73387-52-7 ]
[ 73387-51-6 ]

Reference： [1] Patent: US2014/148461, 2014, A1, . Location in patent: Paragraph 0343-0344
[2] Patent: WO2015/92634, 2015, A1, . Location in patent: Paragraph 00258

2
[ 99-90-1 ]
[ 4637-24-5 ]
[ 60-34-4 ]
[ 73387-52-7 ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: at 110℃; for 4 h; Stage #2: at 25℃;	4-bromoacetophenone (20.0 g; 0.10 mole) and N,N-dimethylformamide dimethylacetal (28.5 mL; 0.20 mole) were mixed together in DMF (12 mL) and heated to 110⁰C for 4 hours. The methanol and water that were generated during the reaction were distilled (6.2 mL). The mixture was cooled to 25°C. Methyl t-butyl ether (100 mL) and methylhydrazine (21.2 mL; 0.40 moles) <n="70"/>were added and the mixture was stirred over night. The reaction mixture was washed with 1 M aqueous ammonium chloride (3 x 40 ml_) and water (40 ml_). The organic phase was dried by azeotropic distillation using a Dean-Stark apparatus. As an alternative to distillation, the solution was dried through an anhydrous magnesium sulfate cartridge. The solution was filtered through a silica gel cartridge (60 g). The product was flushed from the cartridge with methyl t-butyl ether. The fraction(s) containing product were combined and concentrated to about 70 ml_ by distillation. Heptane (120 ml_) was added and distillation was continued until the pot temperature reached 98.4 ⁰C. About 100 ml_ of distillate was collected. The mixture was cooled to 40 ⁰C. The mixture was seeded and the temperature was maintained at 40 ⁰C for 30 minutes while crystallization was initiated. The mixture was slowly chilled to 0 ⁰C over 90 minutes. The mixture was held at 0 ⁰C for 30 minutes. The mixture was filtered and the solid was washed (3 x) with chilled (0⁰C) heptane. The solid was dried on the filter. A cream-colored, crystalline solid (16.3 g; 68percent yield) was obtained. The NMR data of the title compound are as per alternative 1

Reference： [1] Patent: WO2009/69044, 2009, A1, . Location in patent: Page/Page column 67-68
[2] Patent: WO2009/69044, 2009, A1, . Location in patent: Page/Page column 67
[3] Patent: WO2016/16421, 2016, A1, . Location in patent: Page/Page column 52

3
[ 73387-60-7 ]
[ 60-34-4 ]
[ 73387-52-7 ]

Reference： [1] Patent: US2008/125474, 2008, A1, . Location in patent: Page/Page column 14; 16
[2] Patent: US2008/125474, 2008, A1, . Location in patent: Page/Page column 14; 16

4
[ 73387-60-7 ]
[ 60-34-4 ]
[ 73387-52-7 ]

Reference： [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1046 - 1051

5
[ 99-90-1 ]
[ 73387-52-7 ]
[ 73387-51-6 ]

Reference： [1] Patent: US2014/148461, 2014, A1,

6
[ 99-90-1 ]
[ 73387-52-7 ]

Reference： [1] Organic Process Research and Development, 2011, vol. 15, # 5, p. 1046 - 1051

[ 73387-52-7 ] Synthesis Path-Downstream 1~18

1
3-(4'-bromophenyl)-1,1-dimethyl-2-pyrazolinium fluoborate [ No CAS ]
[ 661-36-9 ]
[ 139933-81-6 ]
[ 73387-52-7 ]
[ 54287-94-4 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1992,vol. 31,p. 172 - 176

3
[ 73387-60-7 ]
[ 60-34-4 ]
[ 73387-52-7 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 20 - 75℃; for 5h;Product distribution / selectivity;	Step 3: Preparation of 5-(4-bromophenyl)-1-methyl-1H-pyrazole; Alternative 1; A N,N'-dimethylformamide (15 mL) solution of 4-bromoacetophenone (10.60 g, 53.25 mmols) and N,N'-dimethylformamide dimethyl acetal (2.5 equivalents) was heated at 125 degrees Celcius for 3 hours. The dark red solution was cooled to room temperature. The volatiles were removed by rotary evaporation providing a red viscous oil. To this substance was added anhydrous N,N'-dimethylformamide (15 mL) and methyl hydrazine (7.6 g, 160 mmols, 3 equivalents). The mixture was stirred at room temperature for 1 hour and then heated at 75 degrees Celcius for 4 hours. The volatiles were removed by rotary evaporation and the crude residue was taken up in a small volume of methylene chloride. This red solution was applied to a cartridge of silica gel. The cartridge was eluted with a 20:80 mixture of ethyl acetate and hexanes, respectively. The appropriate fractions were combined and concentrated to produce 12.5 g of a white solid.1H NMR (400 MHz, CHLOROFORM-d) delta ppm 3.87-3.95 (m, J=2.22 Hz, 3H) 6.29-6.36 (m, 1H) 7.31 (dd, J=8.36 Hz, 2H) 7.52-7.56 (m, 1H) 7.62 (dd, J=2.05 Hz, 2H).
	In tert-butyl methyl ether; N,N-dimethyl-formamide; at 25℃;Product distribution / selectivity;	Step 3: Preparation of 5-(4-bromophenyl)-1-methyl-1H-pyrazole; Alternative 2; 4-bromoacetophenone (20.0 g; 0.10 mole) and N,N-dimethylformamide dimethylacetal (28.5 mL; 0.20 mole) were mixed together in DMF (12 mL) and heated to 110 C. for 4 hours. The methanol and water that were generated during the reaction were distilled (6.2 mL). The mixture was cooled to 25 C. Methyl t-butyl ether (100 mL) and methylhydrazine (21.2 mL; 0.40 moles) were added and the mixture was stirred over night. The reaction mixture was washed with 1 M aqueous ammonium chloride (3×40 mL) and water (40 mL). The organic phase was dried by azeotropic distillation using a Dean-Stark apparatus. As an alternative to distillation, the solution was dried through an anhydrous magnesium sulfate cartridge. The solution was filtered through a silica gel cartridge (60 g). The product was flushed from the cartridge with methyl t-butyl ether. The fraction(s) containing product were combined and concentrated to about 70 mL by distillation. Heptane (120 mL) was added and distillation was continued until the pot temperature reached 98.4 C. About 100 mL of distillate was collected. The mixture was cooled to 40 C. The mixture was seeded and the temperature was maintained at 40 C. for 30 minutes while crystallization was initiated. The mixture was slowly chilled to 0 C. over 90 minutes. The mixture was held at 0 C. for 30 minutes. The mixture was filtered and the solid was washed (3×) with chilled (0 C.) heptane. The solid was dried on the filter. A cream-colored, crystalline solid (16.3 g; 68% yield) was obtained. The NMR data of the title compound are as per alternative 1.

Reference： [1]Patent: US2008/125474,2008,A1 .Location in patent: Page/Page column 14; 16
[2]Patent: US2008/125474,2008,A1 .Location in patent: Page/Page column 14; 16

4
[ 1029317-23-4 ]
[ 73387-52-7 ]
[ 1029317-21-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate;tetrakis(triphenylphosphine) palladium(0); bis[2-(diphenylphosphino)phenyl] ether; In tetrahydrofuran; water; isopropyl alcohol; at 90℃; for 4h;Product distribution / selectivity;	Step 4: Preparation of 4-(3-[4-(1-methyl-1H-pyrazol-5-yl)phenyl]thio]phenyl) tetrahydro-2H-pyran-4-carboxamide A mixture of <strong>[73387-52-7]5-(4-bromophenyl)-1-methyl-1H-pyrazole</strong> (0.50 g, 2.10 mmols,), 4-{3-[(tri-isopropylsilyl)thio]phenyl}tetrahydro-2H-pyran-4-carboxamide (0.83 g, 2.10 mmols), Tetrakis(triphenylphosphine)palladium(0) (243 mg, 0.10 equivalents), bis[(2-diphenyl-phosphino)]phenyl ether (113 mg, 0.10 equivalents), and 1.0 M potassium tert-butoxide in THF (6.3 mmols, 3 equivalents) in iPrOH (15 mL) that contained 5% water was heated for 4 hours at 90 degrees Celcius in an atmosphere of nitrogen. The reaction mixture was cooled to room temperature and 7 mL of 1N HCl was added. The product was precipitated by the addition of water (30 mL). The precipitate was collected by suction filtration and washed with water (220 mL) and cold ethyl ether (420 mL). The tan brown solid was dissolved in a small volume of methylene chloride containing 1% methanol and applied to a 140 g cartridge of silica gel. The cartridge was eluted with an acetone:hexane gradient. The appropriate fractions were concentrated and triturated with methanol to produce a white solid (710 mg) as product. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.75-1.84 (m, 3H) 2.40 (d, J=13.54 Hz, 3H) 3.43-3.51 (m, 1H) 3.72 (d, J=11.34 Hz, 3H) 3.84 (s, 3H) 6.40 (d, J=1.46 Hz, 1H) 7.02 (s, 1H) 7.22-7.30 (m, 2H) 7.34 (d, J=8.05 Hz, 1H) 7.38-7.43 (m, 2H) 7.45-7.52 (m, 3H). HRMS calc M+H, 394.1589, found 394.1630.
	With sodium methylate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 2-methyltetrahydrofuran; methanol; at 70℃;Product distribution / selectivity;	Step 4: Preparation of 4-(3-[4-(1-methyl-1H-pyrazol-5-yl)phenyl]thio]phenyl) tetrahydro-2H-pyran-4-carboxamide; Scale-Up Alternative; 4-{3-[(tri-isopropylsilyl)thio]phenyl}tetrahydro-2H-pyran-4-carboxamide (200 g, 0.51 moles), <strong>[73387-52-7]5-(4-bromophenyl)-1-methyl-1H-pyrazole</strong> (126 g, 0.53 moles), and 2-methyltetrahydrofuran (2,000 mL, 10 mL/g of tips carboxamide) were put into the reactor and sparged with nitrogen while heating to 60 C. The sodium methoxide (244.0 mL, 1.07 moles, added as sodium methoxide in methanol solution 25% w/w) was added to the reactor and sparging was continued for another 30 minutes. PdCl2DPPF (3.7 g, 0.005 moles) was added to the reactor and the mixture was heated to 70 C. Once the amount of tips carboxamide was less than 1% of starting amount, the mixture was cooled to 0 C. The mixture was held at 0 C. for one hour. The mixture was filtered and the solid was washed with 2-methyltetrahydrofuran (3×2.5 mL/g). The solid was dried on the filter. The solid was returned to a clean reactor and triturated with water (2,000 mL, 10 mL/g) for two hours at 20 C. The mixture was filtered and the solid was washed with water (2,000 mL, 2×5 mL/g). The solid was dried on the filter. The solid was returned to a clean reactor with the Si-thiol (90.0 g, 0.5 g/g) and THF (about 12.8 L, 70 mL/g). The mixture was heated to 60-65 C. and held for two hours. The mixture was cooled to 25 C. and filtered. The Si-thiol was washed with THF (about 0.9 L, 5 mL/g). The solution was distilled to a concentration of 10 mL/g. The mixture was cooled to 25 C. and hexanes (422.5 mL, 5 mL/g) was added. The mixture was filtered and the solid was washed with hexanes (422.5 mL, 5 mL/g). The solid was dried in a vacuum oven at 70 C.For 2-methyltetrahydrofuran and water, mL/g are referred to grams of tips carboxamide. For Si-thiol, tetrahydrofuran and hexanes, mL/g are referred to grams of title compound.

Reference： [1]Organic process research and development,2011,vol. 15,p. 1046 - 1051
[2]Patent: US2008/125474,2008,A1 .Location in patent: Page/Page column 14; 16-17
[3]Patent: US2008/125474,2008,A1 .Location in patent: Page/Page column 14; 17

5
[ 156275-96-6 ]
[ 73387-52-7 ]
[ 1159186-51-2 ]

Yield	Reaction Conditions	Operation in experiment
		5-(4-bromophenyl)-1 -methyl-1 H-pyrazole (7.84 g), sodium te/f-butoxide (3.81 g), 1 ,1 '-bus(di-i-propylphosphino)ferrocene (332 mg), and palladium acetate (148 mg ) were placed under nitrogen and combined with 60 ml_ anhydrous 1 ,4-dioxane. The resulting mixture was stirred at room temperature for 1 hour before adding thisopropylsilanethiol (7.81 ml) followed by heating at reflux for 1 hour. After cooling to room temperature, the mixture was diluted with ethyl <n="86"/>acetate and washed with water twice and 5% aqueous sodium chloride once. The organic layer was dried over sodium sulfate, filtered, concentrated, and purified by flash chromatography on silica gel to give the title compound. LCMS (M+H): 347; 1 H NMR (400 MHz, DMSO-c/6) delta ppm 0.85- 0.96 (m, 3 H) 0.96 - 1.02 (m, 18 H) 3.84 (s, 3 H) 7.40 (s, 1 H) 7.46 (s, 1 H) 7.58 (d, J=8.32 Hz, 2 H) 7.63 - 7.71 (m, 2 H).

Reference： [1]Patent: WO2009/69044,2009,A1 .Location in patent: Page/Page column 83-84

6
[ 99-90-1 ]
[ 4637-24-5 ]
[ 60-34-4 ]
[ 73387-52-7 ]

Yield	Reaction Conditions	Operation in experiment
68%		4-bromoacetophenone (20.0 g; 0.10 mole) and N,N-dimethylformamide dimethylacetal (28.5 mL; 0.20 mole) were mixed together in DMF (12 mL) and heated to 1100C for 4 hours. The methanol and water that were generated during the reaction were distilled (6.2 mL). The mixture was cooled to 25C. Methyl t-butyl ether (100 mL) and methylhydrazine (21.2 mL; 0.40 moles) <n="70"/>were added and the mixture was stirred over night. The reaction mixture was washed with 1 M aqueous ammonium chloride (3 x 40 ml_) and water (40 ml_). The organic phase was dried by azeotropic distillation using a Dean-Stark apparatus. As an alternative to distillation, the solution was dried through an anhydrous magnesium sulfate cartridge. The solution was filtered through a silica gel cartridge (60 g). The product was flushed from the cartridge with methyl t-butyl ether. The fraction(s) containing product were combined and concentrated to about 70 ml_ by distillation. Heptane (120 ml_) was added and distillation was continued until the pot temperature reached 98.4 0C. About 100 ml_ of distillate was collected. The mixture was cooled to 40 0C. The mixture was seeded and the temperature was maintained at 40 0C for 30 minutes while crystallization was initiated. The mixture was slowly chilled to 0 0C over 90 minutes. The mixture was held at 0 0C for 30 minutes. The mixture was filtered and the solid was washed (3 x) with chilled (00C) heptane. The solid was dried on the filter. A cream-colored, crystalline solid (16.3 g; 68% yield) was obtained. The NMR data of the title compound are as per alternative 1
		A N,N'-dimethylformamide (15 mL) solution of 4-bromoacetophenone (10.60 g, 53.25 mmols) and N,N'-dimethylformamide dimethyl acetal (2.5 equivalents) was heated at 125 degrees Celcius for 3 hours. The dark red solution was cooled to room temperature. The volatiles were removed by rotary evaporation providing a red viscous oil. To this substance was added anhydrous N,N'-dimethylformamide (15 mL) and methyl hydrazine (7.6 g, 160 mmols, 3 equivalents). The mixture was stirred at room temperature for 1 hour and then heated at 75 degrees Celcius for 4 hours. The volatiles were removed by rotary evaporation and the crude residue was taken up in a small volume of methylene chloride. This red solution was applied to a cartridge of silica gel. The cartridge was eluted with a 20:80 mixture of ethyl acetate and hexanes, respectively. The appropriate fractions were combined and concentrated to produce 12.5 g of a white solid. 1 H NMR (400 MHz, CHLOROFORM-c/) delta ppm 3.87 - 3.95 (m, J=2.22 Hz, 3 H) 6.29 - 6.36 (m, 1 H) 7.31 (dd, J=8.36 Hz, 2 H) 7.52 - 7.56 (m, 1 H) 7.62 (dd, J=2.05 Hz, 2 H).
		General procedure for the synthesis of NiTo a stirred solution of 1-(4-bromophenyl)ethan-1-one (30.0 g, 150 mmol) in DMF (18 mL) was added DMFDMA (43.5 mL, 300 mmol), the resulting mixture was stirred at 110 C for 4 hours. After cooling to room temperature, MTBE (150 mL) was added to the mixture, then MeNHNH2 (78.9 g, 600 mmol) was added into above mixture, the resulting mixture was stirred at 25 C for 17 hours. The mixture was diluted with EtOAc (100 mL), filtered and the filter cake was washed with EtOAc (150 mL). The combined organic layer was washed with water (200 mLx3) and brine (200 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford a residue. The residue was purified by flash column chromatography (eluted: PE/EtOAc=8/1 to 4/1) to afford Ni.

Reference： [1]Patent: WO2009/69044,2009,A1 .Location in patent: Page/Page column 67-68
[2]Patent: WO2009/69044,2009,A1 .Location in patent: Page/Page column 67
[3]Patent: WO2016/16421,2016,A1 .Location in patent: Page/Page column 52

7
[ 73387-52-7 ]
[ 1159186-54-5 ]

Yield	Reaction Conditions	Operation in experiment
		Inside an argon filled glove bag, 3.41 g of sodium f-butoxide was placed in an oven-dried flask. 7.03 g of 5-(4-bromophenyl)-1 -methyl-1 /-/-pyrazole, 0.328 g of palladium acetate, and 0.7720 g of 1 ,1 '-bis(di-i-propylphosphino)-ferrocene were added, and the mixture was evacuated/nitrogen filled three times. 50 ml_ of anhydrous 1 ,4-dioxane was added, followed by the addition of 7.00 ml_ of triisopropylsilanethiol. After heating at reflux for 40 minutes, the reaction mixture was cooled, and 20 ml_ of 2.5 N aqueous sodium hydroxide and 15 ml_ of DMSO were then added under nitrogen. The reaction was stirred vigorously at room temperature for 40 minutes and then diluted into ether. The addition of 125 ml_ of 5% aqueous sodium chloride containing ~5 ml_ of concentrated hydrochloric acid adjusted the pH of the aqueous phase to 4, and the mixture was extracted, separated, extracted the aqueous again with ether, combined the ether extracts, dried with magnesium sulfate, filtered, and concentrated to give a dark liquid. The crude product was diluted into ether, extracted twice with 100-mL portions of 0.5 N aqueous sodium hydroxide (discarded the ether), combined the aqueous extracts, extracted the aqueous solution with ether (discarded ether), carefully adjusted the pH to 3 with concentrated hydrochloric acid, extracted three times with ether, combined the ether extracts, dried with magnesium sulfate, filtered, concentrated, and flash chromatographed on silica gel to give 4.4600 gm of product. 1 H NMR (400 MHz, DMSO-c/e) delta ppm 3.83 (s, 3 H) 5.65 (s, 1 H) 6.36 (d, J=1.95 Hz, 1 H) 7.40 (s, 4 H) 7.44 (d, J=1.95 Hz, 1 H).

Reference： [1]Patent: WO2009/69044,2009,A1 .Location in patent: Page/Page column 88

8
[ 1029317-23-4 ]
[ 73387-52-7 ]
C₂₀H₁₈N₄S [ No CAS ]
[ 1331755-98-6 ]

Reference： [1]Organic process research and development,2011,vol. 15,p. 1046 - 1051

9
[ 99-90-1 ]
[ 73387-52-7 ]

Reference： [1]Organic process research and development,2011,vol. 15,p. 1046 - 1051

10
[ 73387-60-7 ]
[ 60-34-4 ]
[ 73387-52-7 ]

Reference： [1]Organic process research and development,2011,vol. 15,p. 1046 - 1051

11
[ 73183-34-3 ]
[ 73387-52-7 ]
[ 1381948-29-3 ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃; for 48h;	In a 40 ml vial, bromo derivative (236 mg, 1.06 mmol, 1.0 eq.), bispinacolotodiboron (253.6 mg, 1.06 mmol, 1.0 eq.), Pd(dppf)CI2 (86.4 mg, 0.106 mmol, 0.1 eq.) and potassium acetate (321.8 mg, 3.17mmol, 3.0 eq.) were mixed in dioxane (10 ml) and heated to 80 C for 48 hours. LCMS indicated that the product was formed in major amount. . The crude reaction was purified in the presence of silica (10-15 gm) and purified using hexanes: ethyl acetate (0-100%) to yield desired boron ester. Theproduct was characterized by reverse phase HPLC using method 4. (ES, m/z) [M +H+] 284.9. Retention time = 1.42 mins

Reference： [1]Patent: WO2014/78813,2014,A1 .Location in patent: Page/Page column 122; 123

12
[ 73387-46-9 ]
[ 74-88-4 ]
[ 73387-52-7 ]
[ 73387-51-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In tetrahydrofuran; at 23℃; for 3h;Inert atmosphere;	(2) 3-(4-bromophenyl)-1-methylpyrazole and 5-(4-bromophenyl)-1-methylpyrazole Sodium hydride (0.43 g, 17.9 mmol) was added slowly to a solution of 3-(4-bromophenyl)-1H-pyrazole (1.0 g, 4.48 mmol) in 50 ml of THF under N2. The mixture was stirred for 1 h, then iodomethane (1.27 g, 8.97 mmol) was added to the suspension. The mixture was stirred at 23 for 2 h. Water (20 mL) was added and extracted with EtAc (50 mL×3). The combined organic phase was washed with brine, dried, concentrated and purified by column chromatography to give 1.0 g of colorless liquid (mixture) (yield: 90%). LC-MS (Method B): m/z 237 (M+H) RT=1.62 min/2.5 min
		Intermediate A4 6-methoxy-2-(4-( 1 -methyl- 1 H-pyrazol-3 -yl)phenyl)-3.4-dihydroisoquinolin- 1 (2H)-one and 6-methoxy-2-(4-(l -methyl- lH-pyrazol-5-yl)phenyl)-3.4-dihydroisoquinolin-l(2H)-one Step 1 : 3-(4-bromophenyl)-lH-pyrazole (0.377 g, 1.690 mmol) was dissolved in THF (8.45 ml). 60% Sodium hydride in oil (0.101 g, 2.54 mmol) was added and the reaction was stirred at rt for 15 min. Methyl iodide (0.116 ml, 1.859 mmol) was added and the reaction was stirred overnight at room temperature. The reaction was quenched with water and extracted three times with dichloromethane. The organic layers were combined, passed through a phase separator and concentrated. The crude material was purified via silica gel chromatography using 0-50% ethyl acetate in heptanes to afford a 2: 1 mixture of products (370 mg, 1.561 mmol, 92 % yield) as a yellow solid. NMR (400 MHz, CHLOROFORM-^ delta ppm 3.86 - 3.95 (m, 3 H), 3.97 (s, 6 H), 6.34 (d, J=1.52 Hz, 1 H), 6.54 (d, J=2.02 Hz, 2 H), 7.30 - 7.33 (m, 2 H), 7.40 (d, J=2.53 Hz, 2 H), 7.49 - 7.56 (m, 5 H), 7.59 - 7.64 (m, 2 H), 7.66 - 7.72 (m, 4 H). LC MS (m/z, MH+): 238.9.

Reference： [1]Patent: US2014/148461,2014,A1 .Location in patent: Paragraph 0343-0344
[2]Patent: WO2015/92634,2015,A1 .Location in patent: Paragraph 00258

13
[ 99-90-1 ]
[ 73387-52-7 ]
[ 73387-51-6 ]

Reference： [1]Patent: US2014/148461,2014,A1

14
C₁₂H₁₄NO₂S^(1-)*Na⁽¹⁺⁾ [ No CAS ]
[ 73387-52-7 ]
[ 1029317-21-2 ]

Reference： [1]Organic Process Research and Development,2015,vol. 19,p. 1944 - 1953

15
[ 68-12-2 ]
[ 73387-52-7 ]
[ 179055-28-8 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure for the synthesis of N2To a stirred solution of Ni (1.20 g, 5.10 mmol) in anhydrous THF (10 mL) was added NaH (240 mg, 6.00 mmol, 60% dispersion in mineral oil), the resulting mixture was stirred at 0 C for 1 hour, then n-BuLi (2.3 mL, 5.75 mmol, 2.5 M in hexane) was added into above mixture at -70 C and stirred at -70 C for 1 hour, freshly distilled DMF (1.85 g, 25.3 mmol) was added into above mixture and stirred at -70 C for 1 hour, then the reaction mixture was allowed to warm to 0 C. TLC showed the reaction was completed. The reaction was quenched with water (30 mL) at 0 C, extracted with EtOAc (30 mLx3). The combined organic phase washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford a residue. The residue was purified by flash column chromatography (eluted: PE/EtOAc=2/1) to afford N2.

Reference： [1]Patent: WO2016/16421,2016,A1 .Location in patent: Page/Page column 52

16
[ 5419-55-6 ]
[ 126-30-7 ]
[ 73387-52-7 ]
5-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)-1-methyl-1H-pyrazole [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 6347 - 6351

17
[ 73387-52-7 ]
C₁₉H₂₈BN₂O₂^(1-)*Li⁽¹⁺⁾ [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 6347 - 6351

18
[ 73387-52-7 ]
1-methyl-5-(4-(trifluoromethylthio)phenyl)-1H-pyrazole [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 6347 - 6351

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H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
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H320	Causes eye irritation
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H332	Harmful if inhaled
H333	May be harmful if inhaled
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H372	Causes damage to organs through prolonged or repeated exposure
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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. 73387-52-7 ] {[proInfo.proName]}

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Water Solubility

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[ 73387-52-7 ] Synthesis Path-Upstream 1~6

[ 73387-52-7 ] Synthesis Path-Downstream 1~18

Related Functional Groups of [ 73387-52-7 ]

Aryls

Bromides

Related Parent Nucleus of [ 73387-52-7 ]

Pyrazoles

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Response

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Disposal

Physical hazards

Health hazards

Environmental hazards

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Related Functional Groups of
[ 73387-52-7 ]

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[ 73387-52-7 ]