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Quality Control of [ 15803-02-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 15803-02-8 ]

Product Citations

Anhydrous and Stereoretentive Fluoride-Enhanced Suzuki–Miyaura Coupling of Immunomodulatory Imide Drug Derivatives

William F. Tracy ; Geraint H. M. Davies ; Lauren N. Grant , et al. JOC,2024,89(7):4595-4606. DOI: 10.1021/acs.joc.3c02873

Abstract: Immunomodulatory imide drugs form

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Product Details of [ 15803-02-8 ]

CAS No. :	15803-02-8	MDL No. :	MFCD02179565
Formula :	C₄H₅BrN₂	Boiling Point :	No data available
Linear Structure Formula :	C₃H₂N₂(CH₃)Br	InChI Key :	IXJSDKIJPVSPKF-UHFFFAOYSA-N
M.W :	161.00	Pubchem ID :	167433
Synonyms :

Calculated chemistry of [ 15803-02-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.25
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	31.19
TPSA :	17.82 ?2

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) :	-6.63 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.63
Log Po/w (XLOGP3) :	0.92
Log Po/w (WLOGP) :	1.18
Log Po/w (MLOGP) :	0.81
Log Po/w (SILICOS-IT) :	1.14
Consensus Log Po/w :	1.14

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.95
Solubility :	1.82 mg/ml ; 0.0113 mol/l
Class :	Very soluble
Log S (Ali) :	-0.88
Solubility :	21.2 mg/ml ; 0.132 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.64
Solubility :	3.71 mg/ml ; 0.023 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.22

Safety of [ 15803-02-8 ]

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

Application In Synthesis of [ 15803-02-8 ]

* 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 [ 15803-02-8 ]
Downstream synthetic route of [ 15803-02-8 ]

[ 15803-02-8 ] Synthesis Path-Upstream 1~1

1
[ 15803-02-8 ]
[ 25015-63-8 ]
[ 942070-88-4 ]
[ 1018975-99-9 ]

Reference： [1] Patent: US2008/91027, 2008, A1, . Location in patent: Page/Page column 6-7

[ 15803-02-8 ] Synthesis Path-Downstream 1~4

1
[ 15803-02-8 ]
[ 591-51-5 ]
[ 84547-84-2 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1959,vol. 625,p. 55,60

2
[ 15803-02-8 ]
[ 78191-00-1 ]
[ 37687-18-6 ]

Yield	Reaction Conditions	Operation in experiment
57%		A. Synthesis of 1-(1-methyl-1H-pyrazol-4-yl)ethanone 4-Bromo-1-methyl-1H-pyrazole (41.3 mL, 400 mmol), was dissolved in tetrahydrofuran (750 mL) and cooled to -78 C. N-Butyllithium (2.5 M solution in hexanes, 160 mL, 400 mmol) was added drop-wise over 30 minutes, and the resulting mixture was stirred for 1 hour at -78 C. After drop-wise addition of a solution of N-methoxy-N-methylacetamide (40.9 mL, 400 mmol) in tetrahydrofuran (100 mL) to the -78 C. reaction mixture, the cooling bath was allowed to warm to 0 C. over 4 hours. The reaction was then quenched with saturated aqueous sodium chloride solution (50 mL), and volatiles were removed in vacuo. The residue was diluted with ethyl acetate (1000 mL), treated with magnesium sulfate, and stirred for 30 minutes before being filtered and concentrated in vacuo. Purification was carried out via silica gel chromatography (material was loaded in a minimum amount of dichloromethane; Gradient: 5% to 100% ethyl acetate in heptane) to provide a pale yellow oil that solidified on standing. Yield: 28.5 g, 230 mmol, 57%. 1H NMR (500 MHz, CDCl3) delta 2.37 (s, 3H), 3.90 (s, 3H), 7.83 (s, 1H), 7.84 (s, 1H).

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 1062 - 1066
Angew. Chem.,2019,vol. 131,p. 1074 - 1078,5
[2]Patent: US2012/214791,2012,A1 .Location in patent: Page/Page column 21
[3]Journal of Medicinal Chemistry,2018,vol. 61,p. 1001 - 1018

3
[ 15803-02-8 ]
[ 850567-56-5 ]
[ 1341981-04-1 ]

Yield	Reaction Conditions	Operation in experiment
44%	With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; water; at 130 - 150℃; for 0.5h;Microwave irradiation;	Preparation 132: 2-Chloro-5-(1 -methyl-1 H-pyrazol-4-yl)aniline; [00302] To a mixture of <strong>[850567-56-5]3-amino-4-chlorophenylboronic acid pinacol ester</strong> (0.1 10g, 0.434 mmol), 4-bromo-1 -methylpyrazole (0.087 g, 0.54 mmol), 1 ,1 '- bis(diphenylphosphino)ferrocene)-dichloropalladium(ll) DCM complex (24 mg, 0.029 mmol) was added anhydrous DME (2.5 mL) followed by 1 M aqueous sodium carbonate (0.99 mL, 0.99 mmol). The microwave vial was heated at 150C for 20 minutes under microwave irradiation. Further catalyst (0.005 g) was added and the vial was heated at 130C for 10 minutes under microwave irradiation. The reaction mixture was partitioned between ethyl acetate (55 mL) and a saturated aqueous NaHC03 solution (15 mL). The organic layer was washed with a saturated aqueous NaHC03 solution (2 x 13 mL), dried (Na2S04) and concentrated in vacuo. This residue was purified using preparative TLC eluting with 30% ethyl acetate in CH2CI2. The product band was recovered and stirred with 2% MeOH in ethyl acetate / CH2CI2 (v/v; 1 :3) (20 mL). The silica was removed by filtration, washed with ethyl acetate / CH2CI2 (v/v; 1 :3) (2 x 5 mL) and acetone (3 x 4 mL) to give the title compound as an off- white solid (0.040 g, 44%). 1 H-NMR (500 MHz, DMSO-d6) 3.84 (s, 3H), 5.29 (s, 2H), 6.72 (dd, J = 2.1 , 8.2 Hz, 1 H), 6.94 (d, J = 2.1 Hz, 1 H), 7.14 (d, J = 8.2 Hz, 1 H), 7.68 (d, J = 0.7 Hz, 1 H), 7.98 (s, 1 H).
44%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,2-dimethoxyethane; water; at 130 - 150℃; for 0.5h;Microwave irradiation;	Preparation 132 2-Chloro-5-(1-methyl-1H-pyrazol-4-yl)aniline To a mixture of <strong>[850567-56-5]3-amino-4-chlorophenylboronic acid pinacol ester</strong> (0.110 g, 0.434 mmol), 4-bromo-1-methylpyrazole (0.087 g, 0.54 mmol), 1,1'-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) DCM complex (24 mg, 0.029 mmol) was added anhydrous DME (2.5 mL) followed by 1M aqueous sodium carbonate (0.99 mL, 0.99 mmol). The microwave vial was heated at 150 C. for 20 minutes under microwave irradiation. Further catalyst (0.005 g) was added and the vial was heated at 130 C. for 10 minutes under microwave irradiation. The reaction mixture was partitioned between ethyl acetate (55 mL) and a saturated aqueous NaHCO3 solution (15 mL). The organic layer was washed with a saturated aqueous NaHCO3 solution (213 mL), dried (Na2SO4) and concentrated in vacuo. This residue was purified using preparative TLC eluting with 30% ethyl acetate in CH2Cl2. The product band was recovered and stirred with 2% MeOH in ethyl acetate/CH2Cl2 (v/v; 1:3) (20 mL). The silica was removed by filtration, washed with ethyl acetate/CH2Cl2 (v/v; 1:3) (25 mL) and acetone (3*4 mL) to give the title compound as an off-white solid (0.040 g, 44%). 1H-NMR (500 MHz, DMSO-d6) 3.84 (s, 3H), 5.29 (s, 2H), 6.72 (dd, J=2.1, 8.2 Hz, 1H), 6.94 (d, J=2.1 Hz, 1H), 7.14 (d, J=8.2 Hz, 1H), 7.68 (d, J=0.7 Hz, 1H), 7.98 (s, 1H).

Reference： [1]Patent: WO2012/123745,2012,A1 .Location in patent: Page/Page column 105-106
[2]Patent: US2013/345181,2013,A1 .Location in patent: Paragraph 0747

4
[ 15803-02-8 ]
[ 124-38-9 ]
[ 84547-84-2 ]

Yield	Reaction Conditions	Operation in experiment
77.3 g	With n-butyllithium; diisopropylamine; In tetrahydrofuran; acetone; at -78 - 0℃; for 1.0h;Inert atmosphere;	tHF (anhydrous) 600 ml was added to a 2 L reaction flask.Diisopropylamine 65.4g,Argon replacement protection,Dry ice acetone was cooled to -78 °C. Add 2.5M n-butyl lithium 258ml,The temperature is raised at 0 ° C for 0.5 h, and the temperature is lowered to -78 ° C.80.0 g of 1-methyl-4-bromopyrazole was added dropwise, and the reaction was maintained at -78 ° C for 1 h.Pass dry carbon dioxide gas until the reaction is complete.TLC showed the reaction was complete, and 1N HCl was added dropwise to adjust pH = 2-3.A large amount of white solid precipitated. After cooling at 0 ° C for 3 h, filter.Drying at 40 ° C for 16 h gave a white solid compound 22 (77.3 g).

Reference： [1]Patent: CN108264520,2018,A .Location in patent: Paragraph 0261; 0262; 0263; 0264; 0265

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Technical Information

? Alkyl Halide Occurrence ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

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