[ CAS No. 590417-95-1 ] {[proInfo.proName]}

Name: 590417-95-1|6-Bromo-2-methyl-2H-indazole|97%
Brand: Ambeed
SKU: A156535
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Quality Control of [ 590417-95-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 590417-95-1 ]

CAS No. :	590417-95-1	MDL No. :	MFCD09870048
Formula :	C₈H₇BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BVYFYDANLZQCPV-UHFFFAOYSA-N
M.W :	211.06	Pubchem ID :	22558624
Synonyms :

Calculated chemistry of [ 590417-95-1 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.12
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	48.7
TPSA :	17.82 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.09
Log Po/w (XLOGP3) :	2.62
Log Po/w (WLOGP) :	2.34
Log Po/w (MLOGP) :	2.19
Log Po/w (SILICOS-IT) :	2.11
Consensus Log Po/w :	2.27

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.4
Solubility :	0.0831 mg/ml ; 0.000394 mol/l
Class :	Soluble
Log S (Ali) :	-2.64
Solubility :	0.479 mg/ml ; 0.00227 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.33
Solubility :	0.0985 mg/ml ; 0.000467 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.58

Safety of [ 590417-95-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 590417-95-1 ]

* 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 [ 590417-95-1 ]
Downstream synthetic route of [ 590417-95-1 ]

[ 590417-95-1 ] Synthesis Path-Upstream 1~6

1
[ 590417-95-1 ]
[ 50593-30-1 ]

Reference： [1] Patent: US2016/229837, 2016, A1,
[2] Patent: CN105461694, 2016, A,

2
[ 74-88-4 ]
[ 590417-94-0 ]
[ 590417-95-1 ]

Yield	Reaction Conditions	Operation in experiment
51%	Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 0.5 h; Stage #2: at 20℃;	Example 402 Part A: To 6-bromoindazole (402A) (5.0 g, 25.4 mmol) in THF (50 mL) was added sodium hydride (95percent, 672 mg, 26.6 mmol) with ice bath cooling. The mixture was stirred for 30 minutes. Methyl iodide (6.36 mL, 102 mmol) was added at room temperature. The reaction mixture was quenched with ammonium chloride solution and the layers were separated. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate and concentrated. Purification by column chromatography (SiO₂, ethyl acetate/hexane gradient) afforded 1-methyl-6-bromoindazole (402B) (2.71 g, 51percent) as a yellow oil and 2-methyl-6- bromoindazole (402C) (2.28 g, 43percent) as a yellow crystalline solid. 402B: HPLC-MS tR = 1.69 min (UV₂54 nm); mass calculated for formulaC₈H₇BrN₂209.98, observed LCMS m/z 211.0 (M+H).402C: HPLC-MS t_R = 1.54 min (UV₂54 nm); mass calculated for formulaC₈H₇BrN₂209.98, observed LCMS m/z 211.0 (M+H).
47%	Stage #1: With sodium methylate In tetrahydrofuran for 0.5 h; Stage #2: at 20℃; for 3 h;	Example 2005 Compound 2005A (400 mg, 2.03 mmol) was dissolved in 10 ml of THF and reacted with sodium methoxide (4 mL, 2.03 mmol). After 30 min iodomethane (0.5 mL, 8.12 mmol) was added. Reaction mixture was stirred for 3 hours at room temp, then it was added to ethyl acetate and water. The aqueous layer was extracted with ethyl acetate twice. All the organic layers were combined, washed with brine solution and dried over sodium sulfate. The solvent was removed by rotary evaporator and further purified by S1O₂ column chromatography to give 2005B (200 mg, 47percent yield), 2005C (150 mg, 35percent yield).

Reference： [1] Patent: WO2007/84451, 2007, A1, . Location in patent: Page/Page column 142
[2] Patent: WO2007/84451, 2007, A1, . Location in patent: Page/Page column 168

3
[ 79762-54-2 ]
[ 74-88-4 ]
[ 590417-94-0 ]
[ 590417-95-1 ]

Reference： [1] Patent: WO2015/42397, 2015, A1, . Location in patent: Paragraph 000898
[2] Patent: WO2015/65937, 2015, A1, . Location in patent: Paragraph 000807

4
[ 74-88-4 ]
[ 590417-94-0 ]
[ 590417-95-1 ]

Yield	Reaction Conditions	Operation in experiment
51%	Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 0.5 h; Stage #2: at 20℃;	Example 402 Part A: To 6-bromoindazole (402A) (5.0 g, 25.4 mmol) in THF (50 mL) was added sodium hydride (95percent, 672 mg, 26.6 mmol) with ice bath cooling. The mixture was stirred for 30 minutes. Methyl iodide (6.36 mL, 102 mmol) was added at room temperature. The reaction mixture was quenched with ammonium chloride solution and the layers were separated. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate and concentrated. Purification by column chromatography (SiO₂, ethyl acetate/hexane gradient) afforded 1-methyl-6-bromoindazole (402B) (2.71 g, 51percent) as a yellow oil and 2-methyl-6- bromoindazole (402C) (2.28 g, 43percent) as a yellow crystalline solid. 402B: HPLC-MS tR = 1.69 min (UV₂54 nm); mass calculated for formulaC₈H₇BrN₂209.98, observed LCMS m/z 211.0 (M+H).402C: HPLC-MS t_R = 1.54 min (UV₂54 nm); mass calculated for formulaC₈H₇BrN₂209.98, observed LCMS m/z 211.0 (M+H).
47%	Stage #1: With sodium methylate In tetrahydrofuran for 0.5 h; Stage #2: at 20℃; for 3 h;	Example 2005 Compound 2005A (400 mg, 2.03 mmol) was dissolved in 10 ml of THF and reacted with sodium methoxide (4 mL, 2.03 mmol). After 30 min iodomethane (0.5 mL, 8.12 mmol) was added. Reaction mixture was stirred for 3 hours at room temp, then it was added to ethyl acetate and water. The aqueous layer was extracted with ethyl acetate twice. All the organic layers were combined, washed with brine solution and dried over sodium sulfate. The solvent was removed by rotary evaporator and further purified by S1O₂ column chromatography to give 2005B (200 mg, 47percent yield), 2005C (150 mg, 35percent yield).

Reference： [1] Patent: WO2007/84451, 2007, A1, . Location in patent: Page/Page column 142
[2] Patent: WO2007/84451, 2007, A1, . Location in patent: Page/Page column 168

5
[ 79762-54-2 ]
[ 74-88-4 ]
[ 590417-94-0 ]
[ 590417-95-1 ]

Reference： [1] Patent: WO2015/42397, 2015, A1, . Location in patent: Paragraph 000898
[2] Patent: WO2015/65937, 2015, A1, . Location in patent: Paragraph 000807

6
[ 74-83-9 ]
[ 590417-95-1 ]

Reference： [1] European Journal of Medicinal Chemistry, 2019, vol. 161, p. 533 - 542

[ 590417-95-1 ] Synthesis Path-Downstream 1~25

1
[ 74-88-4 ]
[ 590417-94-0 ]
[ 590417-95-1 ]

Yield	Reaction Conditions	Operation in experiment
51%; 43%		Example 402 Part A: To 6-bromoindazole (402A) (5.0 g, 25.4 mmol) in THF (50 mL) was added sodium hydride (95percent, 672 mg, 26.6 mmol) with ice bath cooling. The mixture was stirred for 30 minutes. Methyl iodide (6.36 mL, 102 mmol) was added at room temperature. The reaction mixture was quenched with ammonium chloride solution and the layers were separated. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate and concentrated. Purification by column chromatography (SiO2, ethyl acetate/hexane gradient) afforded 1-methyl-6-bromoindazole (402B) (2.71 g, 51percent) as a yellow oil and 2-methyl-6- bromoindazole (402C) (2.28 g, 43percent) as a yellow crystalline solid. 402B: HPLC-MS tR = 1.69 min (UV254 nm); mass calculated for formulaC8H7BrN2209.98, observed LCMS m/z 211.0 (M+H).402C: HPLC-MS tR = 1.54 min (UV254 nm); mass calculated for formulaC8H7BrN2209.98, observed LCMS m/z 211.0 (M+H).
47%; 35%		Example 2005 Compound 2005A (400 mg, 2.03 mmol) was dissolved in 10 ml of THF and reacted with sodium methoxide (4 mL, 2.03 mmol). After 30 min iodomethane (0.5 mL, 8.12 mmol) was added. Reaction mixture was stirred for 3 hours at room temp, then it was added to ethyl acetate and water. The aqueous layer was extracted with ethyl acetate twice. All the organic layers were combined, washed with brine solution and dried over sodium sulfate. The solvent was removed by rotary evaporator and further purified by S1O2 column chromatography to give 2005B (200 mg, 47percent yield), 2005C (150 mg, 35percent yield).

Reference： [1]Patent: WO2007/84451,2007,A1 .Location in patent: Page/Page column 142
[2]Patent: WO2007/84451,2007,A1 .Location in patent: Page/Page column 168

2
[ 590417-95-1 ]
[ 944718-43-8 ]
[ 944718-44-9 ]

Yield	Reaction Conditions	Operation in experiment
76%	With diisopropylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In N,N-dimethyl-formamide; at 70℃; for 17h;	Step 3 A mixture of 2014C (168 mg, 0.56 mmol), 2005C (124 mg, 0.58 mmol), Pd(PPh3)2CI2 (4.0 mg, 6 mmol), CuI (21 mg, 110 mmol), and diisopropylethylamine (0.39 mL, 0.24 mmol) in DMF (4 ml) was purged with N2 and heated to 70 0C. After heating for 17 h, the mixture was cooled to 250C and the mixture was poured to an ice-water. The organic layers were extracted with EtOAc and the combined organic solution was washed with brine solution, dried (Na2SO4), and concentrated in vacuo. The residue was purified by SiO2 column chromatography (1 to 5% MeOH in CH2CI2) to afford racemic 2014D (183 mg, 76% yield). The active enantiomer of 2014D was separated by chiral HPLC on chiral OD column (IPA/hexane = 1 :3) to afford active isomer 2014D (50 mg).

Reference： [1]Patent: WO2007/84451,2007,A1 .Location in patent: Page/Page column 174

4
[ 79762-54-2 ]
[ 74-88-4 ]
[ 590417-94-0 ]
[ 590417-95-1 ]

Yield	Reaction Conditions	Operation in experiment
		[000898] To Compound 232A (10 g, 50.8 mmol) in THF (50 mL) was added sodium hydride (60percent in mineral, 2.2 g, 55.8 mmol) with ice bath cooling. The mixture was stirred at room temperature for 30 min. Methyl iodide (4.74 mL, 76.1 mmol) was added at room temperature. The reaction mixture was stirred at room temperature for 1 h, quenched with saturated aqueous ammonium chloride solution (30 mL), and extracted with ethyl acetate (100 mL x 3). The combined organic layers were washed with brine (200 mL), dried over anhydrous sodium sulfate, and concentrated. Purification with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 10percent to 30percent v/v) gave Compound 232B and Compound 232C.
		[000807j To Compound 132A (10 g, 50.8 mmol) in THF (50 mL) was added sodium hydride (60percent in mineral, 2.2 g, 55.8 mmol) with ice bath cooling. The mixture was stirred at room temperature for 30 mm. Methyl iodide (4.74 mL, 76.1 mmol) was added at room temperature. The reaction mixture was stirred at room temperature for 1 h, quenched with saturated aqueous ammonium chloride solution (30 mL), and extracted with ethyl acetate (100 mL x 3). The combined organic layers were washed with brine (200 mL), dried over anhydrous sodium sulfate, and concentrated. Purification with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 10percent to 30percent v/v) gave Compound 132B and Compound 132C. For Compound 132B: LC-MS (ESI) mlz: 211 [M+H] ?H-NMR (DMSOd 6, 400 MHz): 5 (ppm) 4.04 (s, 3H), 7.26 (dd, J= 8.8, 2.0 Hz, 1H), 7.72 (d, J= 8.4 Hz, 1H), 7.99 (s, 1H), 8.08 (d, J= 0.8 Hz, 1H). For Compound 132C: LC-MS (ESI) mlz: 211 [M+H] ?H-NMR (DMSO-d6, 400 MHz): 5 Qpm) 4.17 (s, 3H), 7.13 (dd, J 8.8, 2.0 Hz, 1H), 7.69 (d, J= 8.8 Hz, 1H), 7.85 (s, 1H), 8.41 (s, 1H).

Reference： [1]Patent: WO2015/42397,2015,A1 .Location in patent: Paragraph 000898
[2]Patent: WO2015/65937,2015,A1 .Location in patent: Paragraph 000807

5
[ 590417-95-1 ]
C₁₆H₂₁BF₂O₄ [ No CAS ]
C₁₆H₁₂F₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,4-dioxane; water; at 100℃; for 4h;Inert atmosphere;	[000907] A mixture of Compound 232C (200 mg, 0.95 mmol), Compound 178C (310 mg, 0.95 mmol), Pd(dppf)Cl2 (39 mg, 0.05 mmol), and K2C03 (393 mg, 2.85 mmol) in dioxane (3 mL) and water (3 mL) was stirred under nitrogen at 100 C for 4 h. The reaction mixture was cooled to room temperature and filtered through celite. The filtrate was treated with water (50 mL) and extracted with ethyl acetate (50 mL x 2). The aqueous layer was acidified to pH 3 with aqueous HCl solution (I N) and extracted with ethyl acetate (100 mL x 2). The combined organic layers were washed with water (50 mL x 2) and brine (50 mL), dried over anhydrous sodium sulfate, and concentrated to give Compound 237A.

Reference： [1]Patent: WO2015/42397,2015,A1 .Location in patent: Paragraph 000907

6
[ 590417-95-1 ]
C₁₆H₂₁BF₂O₄ [ No CAS ]
N-((1R,2R)-1-(3-chloro-4-cyclopropoxyphenyl)-1-hydroxy-3-(pyrrolidin-1-yl)propan-2-yl)-2,2-difluoro-2-(4-(2-methyl-2H-indazol-6-yl)phenyl)acetamide [ No CAS ]

Reference： [1]Patent: WO2015/42397,2015,A1

7
[ 590417-95-1 ]
6-bromo-3-chloro-2-methyl-2H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With sulfuryl dichloride; acetic acid; at 20℃; for 4h;	To a solution of <strong>[590417-95-1]6-bromo-2-methyl-2H-indazole</strong> (1.0 g, 4.7 mmol) inAcOH (10 mL) was added S02C12(0.58 mL, 7.1 mmol). The solution was stirred at rt for 4 h. 2M aq. NaOH (60 mL) was added, and the reaction was extracted with EA (100 mL). Organics were dried over Na2S04, concentrated, and purified by flashchromatography on silica gel (PE /EA = 5/1) to afford 1.1 g (96 %) of the title compound as a yellow solid. [M+H] Calc'd for C8H6BrClN2, 245; Found, 245.

Reference： [1]Patent: WO2016/44138,2016,A1 .Location in patent: Paragraph 00145

8
[ 590417-95-1 ]
3-chloro-N,2-dimethyl-N-phenyl-2H-indazol-6-amine [ No CAS ]

Reference： [1]Patent: WO2016/44138,2016,A1

9
[ 590417-95-1 ]
methyl 3-amino-2-(2-{2-methyl-6-[methyl(phenyl)amino]-2H-indazol-3-yl}ethynyl)pyridine-4-carboxylate [ No CAS ]

Reference： [1]Patent: WO2016/44138,2016,A1

10
[ 590417-95-1 ]
[ 50593-30-1 ]

Reference： [1]Patent: US2016/229837,2016,A1
[2]Patent: CN105461694,2016,A

11
[ 590417-95-1 ]
4-((5-chloro-2-((2-methyl-2H-indazol-6-yl)amino)pyrimidin-4-yl)amino)piperidine-1-carboxylic acid tert-butylester [ No CAS ]

Reference： [1]Patent: US2016/229837,2016,A1
[2]Patent: CN105461694,2016,A

12
[ 590417-95-1 ]
5-chloro-N<SUP>2</SUP>-(2-methyl-2H-indazol-6-yl)-N<SUP>4</SUP>-(piperidin-4-yl)pyrimidine-2,4-diamine [ No CAS ]

Reference： [1]Patent: US2016/229837,2016,A1
[2]Patent: CN105461694,2016,A

13
[ 590417-95-1 ]
6-(4-((5-chloro-2-((2-methyl-2H-indazol-6-yl)amino)pyrimidin-4-yl)amino)piperidin-1-yl)pyridazine-3-carbonitrile [ No CAS ]

Reference： [1]Patent: US2016/229837,2016,A1
[2]Patent: CN105461694,2016,A

14
[ 1013-88-3 ]
[ 590417-95-1 ]
N-(diphenylmethylene)-2-methyl-2H-indazol-6-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98.3%	With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In 1,4-dioxane; at 100℃;Inert atmosphere;	Step 1) N-(diphenylmethylene)-2-methyl-2H-indazol-6-amine To a solution of <strong>[590417-95-1]6-bromo-2-methyl-2H-indazole</strong> (1 g, 4.738 mmol), diphenylmethanimine (1.29 g, 7.12 mmol) and tert-butoxysodium (911 mg, 9.480 mmol) in 1,4-dioxane (25 mL) was added BINAP (295 mg, 0.474 mmol) and Pd2(dba)3 (224 mg, 0.237 mmol). The mixture was degassed for 5 min and refilled with N2. The reaction mixture was stirred at 100 C. overnight then concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v)=10/1 to 1/1) to give the title compound as a yellow solid (1.45 g, yield 98.3%). LC-MS (ESI, pos. ion) m/z: 312.4 [M+H]+.
98.3%	With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In 1,4-dioxane; at 100℃;Inert atmosphere;	6-bromo-2-methyl -2H- indazole (1.0g, 4.738mmol), benzophenone imine (1.29g, 7.12mmol) and sodium tert-butoxide (911mg, 9.480mmol) in 1,4-dioxane (25mL) was added BINAP (295mg, 0.474mmol) and Pd2 (dba) 3 (224 mg, 0.237mmol) reaction system in addition to the air for 5 minutes, then re filled with nitrogen. The resulting reaction mixture was warmed to 100 deg.] C overnight, thenAfter concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (PE / EtOAc (v / v) = 10/1 to 1/1) to give the title compound as a yellow solid(1.45g, yield 98.3%).

Reference： [1]Patent: US2016/229837,2016,A1 .Location in patent: Paragraph 0571; 0572
[2]Patent: CN105461694,2016,A .Location in patent: Paragraph 0738; 0739; 0740

15
[ 74-83-9 ]
6-bromo-1H-indazole [ No CAS ]
[ 590417-95-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;	General procedure: 458 mg (2.0 mmol) of methyl 3-(bromomethyl) benzoate (6a) and 382 mg (2.0 mmol) 6-bromoindole (5a) were added into a 50 mL flask, then 5.0 mL anhydrous DMF and 1.38 g (10.0mmol) potassium carbonate were added. The mixture was stirred at room temperature overnight.TLC indicated no starting material remained and the reaction was quenched by adding 25 mLwater. The solution was extracted with ethyl acetate (30 mL ×3) or dichloromethane (30 mL ×3).The organic solvent was combined and evaporated, the product was purified by flash column chromatography using hexane : ethyl acetate (7:1) as eluent. 655.2 mg target compound obtainedas pale yellow oil, yield 95%.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 161,p. 533 - 542

16
[ 590417-95-1 ]
C₂₅H₂₀FN₃O₂ [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 161,p. 533 - 542

17
[ 590417-95-1 ]
3-fluoro-5-[[6-(2-methylindazol-6-yl)indol-1-yl]methyl]benzoic acid [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 161,p. 533 - 542

18
[ 590417-95-1 ]
[ 147621-18-9 ]
6-(1H-indol-6-yl)-2-methylindazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In 1,4-dioxane; for 4h;Reflux; Inert atmosphere;	General procedure: Indole-6-boronic acid (274 mg, 1.7 mmol) and 7a (516 mg, 1.5 mmol)were added into a 100 mL round-bottom flask containing 1,4-dioxane (10 mL), then 25.2 mgPd(PPh3)2Cl2 was added, followed by 1.0 mL 2.0 M K2CO3. The mixture was stirred and heatedto reflux under Argon for about 4 hours. After the reaction was complete, the mixture was cooledto room temperature, 10.0 mL H2O was added and the product was extracted with ethyl acetate(10 mL×3). The organic solvent was combined, dried (anhydrous Na2SO4), filtered andevaporated. The crude product was purified by chromatographic column using hexane : ethylacetate (4:1) as eluent. 380.1 mg methyl 3-[[6-(1H-indol-6-yl)indol-1-yl]methyl]benzoate wasobtained as pale yellow oil, yield 67%.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 161,p. 533 - 542

19
[ 590417-95-1 ]
[ 106-24-1 ]
C₁₈H₂₄N₂O [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 3541 - 3549

20
[ 590417-95-1 ]
[ 81166-84-9 ]
6-(2-cyclopropylethynyl)-2-methyl-indazole [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 9378 - 9384

21
[ 1687-51-0 ]
[ 590417-95-1 ]
C₁₆H₁₃N₅ [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 6874 - 6878

22
[ 79762-54-2 ]
[ 74-88-4 ]
[ 590417-95-1 ]

Yield	Reaction Conditions	Operation in experiment
49%		Step 1: Preparation of 6-bromo-2-methyl-2H-indazole To a solution of 6-bromo-1H-indazole (6.48 g, 32.9 mmol) in anhydrous tetrahydrofuran (80 mL) at 0 C. was added sodium hydride (60% in mineral oil, 1.39 g, 34.5 mmol). The reaction mixture was warmed to room temperature for 2 h before iodomethane (18.68 g, 131.6 mmol) was added. The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with water (300 mL) and extracted with ethyl acetate (100 mL*3). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by column chromatography (silica, petroleum ether/ethyl acetate=4/1) to give 6-bromo-2-methyl-2H-indazole (3.4 g, 16.11 mmol, 49%) as a yellow oil. LCMS (ESI) m/z: 211.1 [M+H]+.

Reference： [1]Patent: US2019/330198,2019,A1 .Location in patent: Paragraph 1165

23
[ 590417-95-1 ]
[ 126085-91-4 ]
ethyl 5-(2-methyl-2H-indazol-6-yl)isoxazole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; at 90℃; for 16h;Inert atmosphere;	Step 2: Preparation of ethyl 5-(2-methyl-2H-indazol-6-yl)isoxazole-3-carboxylate To a solution of <strong>[590417-95-1]6-bromo-2-methyl-2H-indazole</strong> (0.600 g, 2.84 mmol) in 1,4-dioxane (10 mL) at room temperature was added ethyl 5-(tributylstannyl)isoxazole-3-carboxylate (1.35 g, 3.13 mmol) and bis(triphenylphosphine)palladium(II) dichloride (0.199 g, 0.29 mmol) under nitrogen. The reaction mixture was heated at 90 C. for 16 h. The reaction mixture was cooled to room temperature and diluted with water (100 mL) and extracted with ethyl acetate (50 mL*3). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by column chromatography (silica, petroleum ether/ethyl acetate=5/1) to afford ethyl 5-(2-methyl-2H-indazol-6-yl)isoxazole-3-carboxylate (620 mg, 2.29 mmol, 81%) as a yellow solid. LCMS (ESI) m/z: 272.1 [M+H]+.

Reference： [1]Patent: US2019/330198,2019,A1 .Location in patent: Paragraph 1167

24
[ 590417-95-1 ]
5-(2-methyl-2H-indazol-6-yl)isoxazole-3-carboxylate [ No CAS ]

Reference： [1]Patent: US2019/330198,2019,A1

25
[ 590417-95-1 ]
5-(5-(2-methyl-2H-indazol-6-yl)isoxazol-3-yl)(3-phenylazetidin-1-yl)methanone [ No CAS ]

Reference： [1]Patent: US2019/330198,2019,A1

Same Skeleton Products

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Historical Records

Related Functional Groups of
[ 590417-95-1 ]

Bromides

[ 1146637-10-6 ]

5-Bromo-2,7-dimethyl-2H-indazole

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[ 1159511-89-3 ]

5-Bromo-2,4-dimethyl-2H-indazole

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[ 1191616-45-1 ]

4-(4-Bromophenyl)-1-methyl-1H-pyrazole

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[ 590417-93-9 ]

4-Bromo-2-methyl-2H-indazole

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[ 1159511-86-0 ]

4-Bromo-2,5-dimethyl-2H-indazole

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Related Parent Nucleus of
[ 590417-95-1 ]

Indazoles

[ 1146637-10-6 ]

5-Bromo-2,7-dimethyl-2H-indazole

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[ 1159511-89-3 ]

5-Bromo-2,4-dimethyl-2H-indazole

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[ 590417-93-9 ]

4-Bromo-2-methyl-2H-indazole

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[ 1159511-86-0 ]

4-Bromo-2,5-dimethyl-2H-indazole

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6-Bromo-3-methyl-2H-indazole

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
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

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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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. 590417-95-1 ] {[proInfo.proName]}

Quality Control of [ 590417-95-1 ]

Related Doc. of [ 590417-95-1 ]

Product Details of [ 590417-95-1 ]

Calculated chemistry of [ 590417-95-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 590417-95-1 ]

Application In Synthesis of [ 590417-95-1 ]

[ 590417-95-1 ] Synthesis Path-Upstream 1~6

[ 590417-95-1 ] Synthesis Path-Downstream 1~25

Related Functional Groups of [ 590417-95-1 ]

Bromides

Related Parent Nucleus of [ 590417-95-1 ]

Indazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 590417-95-1 ]

Related Parent Nucleus of
[ 590417-95-1 ]