[ CAS No. 1083181-43-4 ] {[proInfo.proName]}

Name: 1083181-43-4|6-Bromo-1-methyl-1H-benzo[d][1,2,3]triazole|97%
Brand: Ambeed
SKU: A121654
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Quality Control of [ 1083181-43-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1083181-43-4 ]

SDS Specification

Alternatived Products of [ 1083181-43-4 ]

Product Details of [ 1083181-43-4 ]

CAS No. :	1083181-43-4	MDL No. :	MFCD11559050
Formula :	C₇H₆BrN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GPKHIVIGTSWNRM-UHFFFAOYSA-N
M.W :	212.05	Pubchem ID :	53393378
Synonyms :

Calculated chemistry of [ 1083181-43-4 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.14
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	46.49
TPSA :	30.71 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) :	-6.3 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.94
Log Po/w (XLOGP3) :	1.82
Log Po/w (WLOGP) :	1.73
Log Po/w (MLOGP) :	2.08
Log Po/w (SILICOS-IT) :	1.62
Consensus Log Po/w :	1.84

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.91
Solubility :	0.263 mg/ml ; 0.00124 mol/l
Class :	Soluble
Log S (Ali) :	-2.08
Solubility :	1.74 mg/ml ; 0.00823 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.96
Solubility :	0.233 mg/ml ; 0.0011 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.95

Safety of [ 1083181-43-4 ]

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 [ 1083181-43-4 ]

* 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 [ 1083181-43-4 ]
Downstream synthetic route of [ 1083181-43-4 ]

[ 1083181-43-4 ] Synthesis Path-Upstream 1~7

1
[ 74-88-4 ]
[ 191230-40-7 ]
[ 1083181-43-4 ]
[ 944718-31-4 ]

Yield	Reaction Conditions	Operation in experiment
25%	Stage #1: With sodium methylate In tetrahydrofuran for 0.5 h; Stage #2: at 20℃; for 4 h;	Example 2003 Compound 2003A (400 mg, 2.0 mmol) was dissolved in 10 mL of THF and reacted with sodium methoxide (4 mL, 2.0 mmol). After 30 min iodomethane (0.5 mL, 8.0 mmol) was added. Reaction mixture was stirred for 4 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 Siψ₂ column chromatography to give 2003B (105 mg, 25percent yield), 2003C (110 mg, 26percent yield) and 2003D (106 mg, 25percent yield).

Reference： [1] Patent: WO2007/84451, 2007, A1, . Location in patent: Page/Page column 167

2
[ 32046-62-1 ]
[ 74-88-4 ]
[ 1083181-43-4 ]
[ 944718-31-4 ]

Yield	Reaction Conditions	Operation in experiment
29%	With potassium carbonate; potassium iodide In acetone at 20℃; for 48.25 h; Inert atmosphere; Cooling with ice	A flask equipped with a stirring bar and flushed with Ar is loaded with 5- bromo-1 - -benzotriazole (200 mg; 1.01 mmol; 1 eq.), potassium iodide (17 mg; 0.10 mmol; 0.10 eq.), potassium carbonate (698 mg; 5.05 mmol; 5 eq.) and acetone (20 ml_). The mixture is cooled in an ice bath and iodomethane (0.08 mL; 1.11 mmol; 1.10 eq.) is added via syringe. After 15 minutes, the bath is removed and the mixture is stirred for 48 h at room temperature. The reaction mixture is then filtered, and the filtrate is evaporated in vacuo. The residue is purified by FCC (0-30percent EtOAc gradient in hexane) to provide two regioisomers: 5-bromo-1 -methyl-1 H-1 ,2,3-benzotriazole (79, 63 mg, 0.30 mmol, 29percent; UPLC purity: 100percent). 6-bromo-1 -methyl-1 H-1 ,2,3-benzotriazole (80, 57 mg, 0.27 mmol, 27percent; UPLC purity: 100percent).

Reference： [1] Patent: WO2016/180537, 2016, A1, . Location in patent: Page/Page column 253; 254

3
[ 337915-79-4 ]
[ 1083181-43-4 ]

Reference： [1] Patent: WO2011/12622, 2011, A1, . Location in patent: Page/Page column 68; 69

4
[ 321-23-3 ]
[ 1083181-43-4 ]

Reference： [1] Patent: WO2011/12622, 2011, A1,

5
[ 302800-13-1 ]
[ 1083181-43-4 ]

Reference： [1] Patent: WO2011/12622, 2011, A1,

6
[ 74-88-4 ]
[ 191230-40-7 ]
[ 1083181-43-4 ]
[ 944718-31-4 ]

Yield	Reaction Conditions	Operation in experiment
25%	Stage #1: With sodium methylate In tetrahydrofuran for 0.5 h; Stage #2: at 20℃; for 4 h;	Example 2003 Compound 2003A (400 mg, 2.0 mmol) was dissolved in 10 mL of THF and reacted with sodium methoxide (4 mL, 2.0 mmol). After 30 min iodomethane (0.5 mL, 8.0 mmol) was added. Reaction mixture was stirred for 4 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 Siψ₂ column chromatography to give 2003B (105 mg, 25percent yield), 2003C (110 mg, 26percent yield) and 2003D (106 mg, 25percent yield).

Reference： [1] Patent: WO2007/84451, 2007, A1, . Location in patent: Page/Page column 167

7
[ 32046-62-1 ]
[ 74-88-4 ]
[ 1083181-43-4 ]
[ 944718-31-4 ]

Yield	Reaction Conditions	Operation in experiment
29%	With potassium carbonate; potassium iodide In acetone at 20℃; for 48.25 h; Inert atmosphere; Cooling with ice	A flask equipped with a stirring bar and flushed with Ar is loaded with 5- bromo-1 - -benzotriazole (200 mg; 1.01 mmol; 1 eq.), potassium iodide (17 mg; 0.10 mmol; 0.10 eq.), potassium carbonate (698 mg; 5.05 mmol; 5 eq.) and acetone (20 ml_). The mixture is cooled in an ice bath and iodomethane (0.08 mL; 1.11 mmol; 1.10 eq.) is added via syringe. After 15 minutes, the bath is removed and the mixture is stirred for 48 h at room temperature. The reaction mixture is then filtered, and the filtrate is evaporated in vacuo. The residue is purified by FCC (0-30percent EtOAc gradient in hexane) to provide two regioisomers: 5-bromo-1 -methyl-1 H-1 ,2,3-benzotriazole (79, 63 mg, 0.30 mmol, 29percent; UPLC purity: 100percent). 6-bromo-1 -methyl-1 H-1 ,2,3-benzotriazole (80, 57 mg, 0.27 mmol, 27percent; UPLC purity: 100percent).

Reference： [1] Patent: WO2016/180537, 2016, A1, . Location in patent: Page/Page column 253; 254

[ 1083181-43-4 ] Synthesis Path-Downstream 1~18

1
[ 74-88-4 ]
[ 191230-40-7 ]
[ 1083181-43-4 ]
[ 944718-31-4 ]

Yield	Reaction Conditions	Operation in experiment
26%; 25%; 25%		Example 2003 Compound 2003A (400 mg, 2.0 mmol) was dissolved in 10 mL of THF and reacted with sodium methoxide (4 mL, 2.0 mmol). After 30 min iodomethane (0.5 mL, 8.0 mmol) was added. Reaction mixture was stirred for 4 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 Sitheta2 column chromatography to give 2003B (105 mg, 25% yield), 2003C (110 mg, 26% yield) and 2003D (106 mg, 25% yield).

Reference： [1]Patent: WO2007/84451,2007,A1 .Location in patent: Page/Page column 167

2
[ 337915-79-4 ]
[ 1083181-43-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen bromide; sodium nitrite; In water; at 0 - 20℃; for 4.5h;	To a cooled (0 0C) and stirred suspension of (2-amino-5-bromophenyl)methylamine (9.5g, may be prepared as described in intermediate 46) in 2M hydrobromic acid was added dropwise a cooled (5 0C) solution of sodium nitrite (4.02 g) in water (50 ml). The resultant mixture was stirred at 5 0C for 0.5 hr and then at 15-20 0C for 4 hr. The mixture was partitioned between EtOAc (500 ml) and saturated aqueous sodium bicarbonate (500 ml). The aqueous phase was separated off and extracted with EtOAc (500 ml). The organic phases were combined, washed with water and brine, dried (magnesium sulphate) and adsorbed on to silica gel prior to flash chromatography over silica gel, eluting with EtOAc / cyclohexane (1 :3). Fractions containing the target compound were combined and evaporated to give a brown solid (4.48 g). 2.61 g of this was further purified by chromatography over silica gel, eluting with 2% MeOH in chloroform. The appropriate fractions were combined and evaporated to give the target compound as a pale brown solid (1.3O g).

Reference： [1]Patent: WO2011/12622,2011,A1 .Location in patent: Page/Page column 68; 69

3
[ 321-23-3 ]
[ 1083181-43-4 ]

Reference： [1]Patent: WO2011/12622,2011,A1

4
[ 1083181-43-4 ]
[ 107-31-3 ]
[ 120321-73-5 ]

Yield	Reaction Conditions	Operation in experiment
		To a cooled (-78 0C) and stirred solution of 6-bromo-1-methyl-1 H-1 ,2,3-benzotriazole (0.25 g, may be prepared as described in intermediate 47) in dry THF was added a solution of tert-butyllithium in pentane (0.83 ml, 1.7M). This mixture was stirred at -78 0C for 1 hr and then methyl formate (0.036 ml, Aldrich) was added. The mixture was stirred at -78 0C for 0.5 hr and then allowed to warm to room temperature. The reaction was quenched with water and acidified with a few drops of 2N hydrochloric acid. The resultant mixture was extracted with EtOAc (2 x 50 ml), the extracts were combined, washed with water, dried (magnesium sulphate) and evaporated to give a brown oil (0.22 g). This was purified by flash chromatography over silica gel eluting with cyclohexane / EtOAc 50 to 100% to give the target compound (0.017 g) as a brown oil.

Reference： [1]Patent: WO2011/12622,2011,A1 .Location in patent: Page/Page column 69

5
[ 302800-13-1 ]
[ 1083181-43-4 ]

Reference： [1]Patent: WO2011/12622,2011,A1

6
[ 1083181-43-4 ]
N-(4-methanesulfonylpyridin-3-yl)-8-(1-methyl-1H-1,2,3-benzotriazol-6-yl)quinoxalin-6-amine [ No CAS ]

Reference： [1]Patent: WO2016/180537,2016,A1
[2]ChemMedChem,2019,vol. 14,p. 169 - 181

7
[ 1083181-43-4 ]
[ 73183-34-3 ]
[ 1362243-56-8 ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 90℃;Inert atmosphere;	The title compound is prepared according to General Procedure 8 described for Intermediate 14, using 6-bromo-1-methyl-1 H-1 ,2,3-benzotriazole (Intermediate 80, 45 mg; 0.21 mmol; 1 eq.), bis(pinacolato)diboron (108 mg; 0.42 mmol; 2 eq.), potassium acetate (125 mg; 1.27 mmol; 6 eq.), Pd(dppf)CI2 (27 mg; 0.03 mmol; 0.15 eq.) in DMSO (2 mL). Conditions: 90 C overnight. The crude 1-methyl-6-(tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 - - 1 ,2,3-benzotriazole (80 mg; 0.10 mmol; 45%; brown solid; UPLC purity: 85%) is used in the next step without further purification.

Reference： [1]Patent: WO2016/180537,2016,A1 .Location in patent: Page/Page column 254; 255
[2]ChemMedChem,2019,vol. 14,p. 169 - 181

8
[ 32046-62-1 ]
[ 74-88-4 ]
[ 1083181-43-4 ]
[ 944718-31-4 ]

Yield	Reaction Conditions	Operation in experiment
27%; 29%	With potassium carbonate; potassium iodide; In acetone; at 20℃; for 48.25h;Inert atmosphere; Cooling with ice;	A flask equipped with a stirring bar and flushed with Ar is loaded with 5- bromo-1 - -benzotriazole (200 mg; 1.01 mmol; 1 eq.), potassium iodide (17 mg; 0.10 mmol; 0.10 eq.), potassium carbonate (698 mg; 5.05 mmol; 5 eq.) and acetone (20 ml_). The mixture is cooled in an ice bath and iodomethane (0.08 mL; 1.11 mmol; 1.10 eq.) is added via syringe. After 15 minutes, the bath is removed and the mixture is stirred for 48 h at room temperature. The reaction mixture is then filtered, and the filtrate is evaporated in vacuo. The residue is purified by FCC (0-30% EtOAc gradient in hexane) to provide two regioisomers: 5-bromo-1 -methyl-1 H-1 ,2,3-benzotriazole (79, 63 mg, 0.30 mmol, 29%; UPLC purity: 100%). 6-bromo-1 -methyl-1 H-1 ,2,3-benzotriazole (80, 57 mg, 0.27 mmol, 27%; UPLC purity: 100%).

Reference： [1]Patent: WO2016/180537,2016,A1 .Location in patent: Page/Page column 253; 254

9
[ 1083181-43-4 ]
1-[(4-methoxyphenyl)methyl]-1H-pyrazolo[4,3-b]pyridin-3-amine [ No CAS ]
C₁₃H₁₁N₇ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2641 - 2646

10
[ 1083181-43-4 ]
[ 81166-84-9 ]
6-(2-cyclopropylethynyl)-1-methylbenzotriazole [ No CAS ]

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

11
[ 1083181-43-4 ]
[ 201230-82-2 ]
[ 114408-87-6 ]

Yield	Reaction Conditions	Operation in experiment
82%	With N,N,N,N,-tetramethylethylenediamine; palladium diacetate; catacxium A In toluene at 80℃; for 16h; Autoclave;	A9.1 A9.1 : 3-Methyl-3H-benzotriazole-5-carbaldehyde Preparation as described for intermediate A3.1 using 6-Bromo-1 -methyl-1 H- 30 benzotriazole (7.70 g; 36.289 mmol), palladium(ll)-acetate (47% Pd; 162.9 mg; 0.726 mmol), CataCXium A (650.6 mg; 1.814 mmol) N,N,N',N'-tetra- methylethylendiamine (2.74 g; 23.588 mmol) in toluene (100 mL) with CO (4.5 bar) at 80 °C for 16 h. Yield: 4.79 g (82%) brown solid; LC/MS (A): Rt: 1.37 ,, min; (M+H) 162.0.

Reference： [1]Current Patent Assignee: MERCK KGAA - WO2020/114892, 2020, A1 Location in patent: Page/Page column 40-41; 45

12
[ 1083181-43-4 ]
[ 120321-73-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: tert.-butyl lithium / tetrahydrofuran; hexane / -78 °C 1.2: 5.5 h / -78 - 15 °C 2.1: sodium tetrahydroborate; methanol / 1 h / 0 - 15 °C

Reference： [1]Current Patent Assignee: CASE WESTERN RESERVE UNIVERSITY - WO2021/2986, 2021, A2

13
[ 1083181-43-4 ]
6-(chloromethyl)-1-methylbenzotriazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: tert.-butyl lithium / tetrahydrofuran; hexane / -78 °C 1.2: 5.5 h / -78 - 15 °C 2.1: sodium tetrahydroborate; methanol / 1 h / 0 - 15 °C 3.1: methanesulfonyl chloride; triethylamine / dichloromethane / 1 h / 0 - 15 °C

Reference： [1]Current Patent Assignee: CASE WESTERN RESERVE UNIVERSITY - WO2021/2986, 2021, A2

14
[ 1083181-43-4 ]
6-[[4-(2-chlorophenyl)-5-cyclopropylimidazol-1-yl]methyl]-1-methylbenzotriazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: tert.-butyl lithium / tetrahydrofuran; hexane / -78 °C 1.2: 5.5 h / -78 - 15 °C 2.1: sodium tetrahydroborate; methanol / 1 h / 0 - 15 °C 3.1: methanesulfonyl chloride; triethylamine / dichloromethane / 1 h / 0 - 15 °C 4.1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: CASE WESTERN RESERVE UNIVERSITY - WO2021/2986, 2021, A2

15
[ 1083181-43-4 ]
[ 107-31-3 ]
[ 114408-87-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 6-bromo-1-methyl-1H-1,2,3-benzotriazole With tert.-butyl lithium In tetrahydrofuran; hexane at -78℃; Stage #2: Methyl formate In tetrahydrofuran; hexane at -78 - 15℃; for 5.5h;	50 To a -78°C stirred solution of 6-bromo-l-methyl-benzotriazole (300 mg, 1.41 mmol, 1 eq) in THF (5 mL) was added t-BuLi (1.3 M, 1.31 mL, 1.2 eq) (in hexane) dropwise, the mixture was stirred at -78°C for 1 hr. Then methyl formate (424.80 mg, 7.07 mmol, 429.09 uL, 5 eq) was added at -78°C dropwise. The mixture was stirred at -78°C for 0.5 hr and then allowed to warm to 15°C for 5 hrs. The reaction mixture was quenched by addition saturated aq.NH4Cl (5mL), adjusted to pH = 3 by 2N HC1, and extracted with EtOAc (5 mL * 3). The combined organic layers were washed with brine (5 mL * 2), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue to give 3-methylbenzotria zole-5-carbaldehyde (200 mg, crude) was obtained as a brown oil. ESI [M+H] = 162.1.

Reference： [1]Current Patent Assignee: CASE WESTERN RESERVE UNIVERSITY - WO2021/2986, 2021, A2 Location in patent: Paragraph 00488

16
[ 1083181-43-4 ]
[5-[3-chloro-6-fluoro-2-[(E)-2-(6-methyl-4,8-dioxo-1,3,6,2-dioxazaborocan-2- yl)vinyl]phenyl]-1,3-dimethyl-6-oxopyridazin-4-yl] 2-methylpropanoate [ No CAS ]
[5-[3-chloro-6-fluoro-2-[(E)-2-(3-methylbenzotriazol-5-yl)vinyl]phenyl]-1,3-dimethyl-6-oxo-pyridazin-4-yl] 2-methylpropanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ In 2-methyltetrahydrofuran; water at 120℃; for 1h; Inert atmosphere; Microwave irradiation;	3.3.2 3.2 [5-[3-chloro-6-fluoro-2-[(E)-2-(3-methylbenzotriazol-5-yl)vinyl]phenyl]-1 ,3-dimethyl- 6-oxo-pyridazin-4-yl] 2-methylpropanoate (4.343) [5-[3-Chloro-6-fluoro-2-[(E)-2-(6-methyl-4,8-dioxo-1 ,3,6,2-dioxazaborocan-2-yl)vinyl]phenyl]-1 ,3- dimethyl-6-oxo-pyridazin-4-yl] 2-methylpropanoate (700 mg, 1 .35 mmol), 1 ,1 - bis(diphenylphosphino)ferrocene]dichloropalladium(ll) dichloromethane complex[PdCI2(dppf).DCM] (55 mg, 0.067 mmol), 6-bromo-1 -methyl-benzotriazole (371 mg, 1 .75 mmol) and potassium phosphate (1 .17 g, 5.39 mmol) were added to a 10-20ml microwave vial. 2- methyltetrahydrofuran (10 ml) and water (0.5 ml) were added then the reaction mixture degassed by evacuation and back-filling with nitrogen (X3). The reaction mixture was heated 120°C for 60 mins under microwave irradiation.The reaction mixture was filtered through a plug of celite, washing through with EtOAc & EtOH. The filtrate was concentrated under reduced pressure to give a brown gum (853 mg). The crude material was purified by automated flash chromatography on silica gel eluting with a cyclohexane/ethyl acetate gradient to give [5-[3-chloro-6-fluoro-2-[(E)-2-(3-methylbenzotriazol-5- yl)vinyl]phenyl]-1 ,3-dimethyl-6-oxo-pyridazin-4-yl] 2-methylpropanoate (4.343) as an orange gum (622 mg, 87% yield)The purified material was dissolved in acetonitrile (10 ml) and treated with SiliCycle SiliaMetS Thiol (SH) metal scavenger resin (622 mg) at room temperature. The suspension was stirred at room temperature for 1 .5 h, then filtered to remove the resin, washing with further acetonitrile. The filtrate was concentrated in vacuo to provide [5-[3-chloro-6-fluoro-2-[(E)-2-(3-methylbenzotriazol- 5-yl)vinyl]phenyl]-1 ,3-dimethyl-6-oxo-pyridazin-4-yl] 2-methylpropanoate (4.343) as a white solid (583 mg, 87% yield) chloroform) 7.96 (d, J=9.0 Hz,1 H), 7.39 - 7.49 (m, 3H), 7.15 (d, J=16.3 Hz,1 H), 7.05 (t, J=8.7 Hz, 1 H), 6.81 (d, J=16.3 Hz, 1 H), 4.29 (s, 3H), 3.68 (s, 3H), 2.67(spt, J=7.0 Hz, 1 H), 2.23 (s, 3H), 1 .13 (d, J=7.0 Hz, 3H), 1 .09 (d, J=7.0 Hz, 3H)

Reference： [1]Current Patent Assignee: SINOCHEM HOLDINGS CORPORATION LTD; Syngenta (in: Sinochem Holdings) - WO2021/9335, 2021, A1 Location in patent: Page/Page column 53-55

17
[ 1083181-43-4 ]
[ 139301-27-2 ]
C₁₄H₁₀F₃N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
103.5 mg	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 90℃; for 16h;	8 A mixture of 6-bromo-1-methyl-benzotriazole (200 mg, 0.9400 mmol), [4-(trifluoromethoxy)phenyl]boronic acid (233.07 mg, 1.13 mmol), K2CO3 (260.32 mg, 1.89 mmol) and Pd(dppf)Cl2.CH2Cl2 (154.04 mg, 0.19 mmol) in 1,4-Dioxane (6 mL) and Water (0.50 mL) was stirred at 90° C. for 16 hours. After cooling to r.t., the mixture was concentrated to give the crude product. The crude product was purified by Prep-HPLC (water (0.05% ammonia hydroxide v/v)-ACN) to give compound 8 (103.5 mg, 0.35 mmol) as a solid. 1H NMR (400 MHz, DMSO-d6) δH 8.19 (s, 1H), 8.12 (d, 1H), 7.93 (d, 2H), 7.73 (d, 1H), 7.52 (d, 2H), 4.36 (s, 3H). LCMS Rt=1.150 min in 2.0 min chromatography, MS ESI calcd. for C14HuF3N3O [M+H]+ 294.1, found 293.9.
103.5 mg	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 90℃; for 16h;	8 A mixture of 6-bromo-1-methyl-benzotriazole (200 mg, 0.9400 mmol), [4-(trifluoromethoxy)phenyl]boronic acid (233.07 mg, 1.13 mmol), K2CO3 (260.32 mg, 1.89 mmol) and Pd(dppf)Cl2.CH2Cl2 (154.04 mg, 0.19 mmol) in 1,4-Dioxane (6 mL) and Water (0.50 mL) was stirred at 90° C. for 16 hours. After cooling to r.t., the mixture was concentrated to give the crude product. The crude product was purified by Prep-HPLC (water (0.05% ammonia hydroxide v/v)-ACN) to give compound 8 (103.5 mg, 0.35 mmol) as a solid. 1H NMR (400 MHz, DMSO-d6) δH 8.19 (s, 1H), 8.12 (d, 1H), 7.93 (d, 2H), 7.73 (d, 1H), 7.52 (d, 2H), 4.36 (s, 3H). LCMS Rt=1.150 min in 2.0 min chromatography, MS ESI calcd. for C14HuF3N3O [M+H]+ 294.1, found 293.9.

Reference： [1]Current Patent Assignee: PRAXIS PRECISION MEDICINES INC - US2021/355118, 2021, A1 Location in patent: Paragraph 0303; 0309
[2]Current Patent Assignee: PRAXIS PRECISION MEDICINES INC - US2021/355118, 2021, A1 Location in patent: Paragraph 0303; 0309

18
4-bromo-N₂-methyl-benzene-1,2-diamine nitrite [ No CAS ]
[ 1083181-43-4 ]

Yield	Reaction Conditions	Operation in experiment
500 mg	With hydrogenchloride; sodium nitrite In water at 20℃; for 2h;	8 To a solution of 4-bromo-N2-methyl-benzene-1,2-diamine nitrite (960 mg, 3.55 mmol) in HCl (20 mL, 1M, 20 mmol) was added NaNO2 (411 mg, 5.2 mmol), and the mixture was stirred at 20° C. for 2 hours. (0308) The mixture was poured into water (20 mL), extracted with EtOAc (50 mL×2). The combined organic phase was washed with brine (10 mL), dried over Na2SO4, filtered and concentrated to give the crude product. The crude product was purified by silica gel column (EtOAc in PE=20% to 40% to 60%) to give the product (500 mg, 2.26 mmol) as a solid. LCMS Rt=0.700 min in 1.5 min chromatography, MS ESI calcd. for C7H7BrN3 [M+H+2]+ 214.0, found 213.7.
500 mg	With hydrogenchloride; sodium nitrite In water at 20℃; for 2h;	8 To a solution of 4-bromo-N2-methyl-benzene-1,2-diamine nitrite (960 mg, 3.55 mmol) in HCl (20 mL, 1M, 20 mmol) was added NaNO2 (411 mg, 5.2 mmol), and the mixture was stirred at 20° C. for 2 hours. (0308) The mixture was poured into water (20 mL), extracted with EtOAc (50 mL×2). The combined organic phase was washed with brine (10 mL), dried over Na2SO4, filtered and concentrated to give the crude product. The crude product was purified by silica gel column (EtOAc in PE=20% to 40% to 60%) to give the product (500 mg, 2.26 mmol) as a solid. LCMS Rt=0.700 min in 1.5 min chromatography, MS ESI calcd. for C7H7BrN3 [M+H+2]+ 214.0, found 213.7.

Reference： [1]Current Patent Assignee: PRAXIS PRECISION MEDICINES INC - US2021/355118, 2021, A1 Location in patent: Paragraph 0303; 0307-0308
[2]Current Patent Assignee: PRAXIS PRECISION MEDICINES INC - US2021/355118, 2021, A1 Location in patent: Paragraph 0303; 0307-0308

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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. 1083181-43-4 ] {[proInfo.proName]}

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[ 1083181-43-4 ] Synthesis Path-Upstream 1~7

[ 1083181-43-4 ] Synthesis Path-Downstream 1~18

Related Functional Groups of [ 1083181-43-4 ]

Bromides

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Other Aromatic Heterocycles

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[ 1083181-43-4 ]

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[ 1083181-43-4 ]