668970-91-0|4-Ethynyl-3,5-dimethylisoxazole| Ambeed

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Quality Control of [ 668970-91-0 ] Purity: 97% SDS Specification

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Product Details of [ 668970-91-0 ]

CAS No. :	668970-91-0
Formula :	C₇H₇NO
M.W :	121.14
SMILES Code :	CC1=C(C#C)C(C)=NO1
MDL No. :	MFCD08703589
InChI Key :	VRIFFHHNSRUZNX-UHFFFAOYSA-N
Pubchem ID :	53426609

Safety of [ 668970-91-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 668970-91-0 ]

* 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.

Downstream synthetic route of [ 668970-91-0 ]

[ 668970-91-0 ] Synthesis Path-Downstream 1~15

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References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5966 - 5970.

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4-(5-bromo-1H-indol-2-yl)-3,5-dimethylisoxazole [ No CAS ]

References: [1]Patent: US2013/158049,2013,A1 .

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Yield	Reaction Conditions	Operation in experiment
81.0%	With methanol; potassium carbonate; at 20℃; for 72h;	To a solution of 3,5-dimethyl-4-((trimethylsilyl)ethynyl)isoxazole (6.64 g, 34.3 mmol, Eq: 1.00) in methanol (229 ml) was added potassium carbonate (7.12 g, 51.5 mmol, Eq: 1.5). The mixture was stirred at room temperature for 72 hr, before the methanol was removed. The resulting residue was redissolved in ether and washed with water. The water layer was extracted with ether (3) and DCM (1). The combined organics were dried over MgSO4, filtered, and concentrated in vacuo to give 4-ethynyl-3,5-dimethylisoxazole (3.37 g, 27.8 mmol, 81.0% yield) as a brown semi-solid.
31%	With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20℃; for 0.5h;	Tetra-/V-butylammonium fluoride (1 .0M) solution in tetrahydrofurane (24.8 ml_, 24.8 mmol, 1 .5 eq.) was added dropwise to a solution of compound 65 (3.2 g, 16.60 mmol, 1 .0 eq.) in tetrahydrofurane (100 ml_). Reaction mixture was stirred at room temperature for 30 min. Solvents were evaporated under vacuum and the residue was purified by flash chromatography [Biotage ; column AIT 120g; eluant: Cyclohexane/ EtOAc; gradient: 100/0 -> 80/20 (12CV)] affording compound 66 (620 mg, 31 % yield) as a white solid.

References: [1]Patent: US2013/158049,2013,A1 .Location in patent: Paragraph 0261.
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 10045 - 10065.
[3]Patent: WO2019/243273,2019,A1 .Location in patent: Page/Page column 100-101.
[4]MedChemComm,2019,vol. 10,p. 263 - 267.

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References: [1]Patent: US2013/158049,2013,A1 .
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 10045 - 10065.
[3]MedChemComm,2019,vol. 10,p. 263 - 267.
[4]Patent: WO2019/243273,2019,A1 .

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Yield	Reaction Conditions	Operation in experiment
98.6%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In tetrahydrofuran; at 80℃; for 3h;	To a solution of 4-bromo-2-iodoaniline (2.5 g, 8.39 mmol, Eq: 1.00) and <strong>[668970-91-0]4-ethynyl-3,5-dimethylisoxazole</strong> (1.22 g, 10.1 mmol, Eq: 1.2) in triethylamine (16.8 ml, 8.39 mmol, Eq: 1.00) and THF (33.6 ml) was added tetrakis(triphenylphosphine)palladium (0) (485 mg, 420 μmol, Eq: 0.05) and copper (I) iodide (37.6 mg, 420 μmol, Eq: 0.05). This mixture was heated to 80 C. for 3 h, before the solvent were removed. The resulting residue was redissolved in ethyl acetate and washed with water and brine. The organic layer was dried onto silica gel and purified by flash chromatography (5-50% ethyl acetate/hexane gradient) to give 4-bromo-2-((3,5-dimethylisoxazol-4-yl)ethynyl)aniline (2.41 g, 8.28 mmol, 98.6% yield) as a brown solid.

References: [1]Patent: US2013/158049,2013,A1 .Location in patent: Paragraph 0262.

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