1083168-84-6|2-Methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine| Ambeed

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Quality Control of [ 1083168-84-6 ] Purity: 98% SDS Specification

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Product Details of [ 1083168-84-6 ]

CAS No. :	1083168-84-6
Formula :	C₁₃H₂₀BNO₃
M.W :	249.11
SMILES Code :	CC1(C)C(C)(C)OB(C2=CC(C)=CN=C2OC)O1
MDL No. :	MFCD12923399
InChI Key :	BMIBJCFFZPYJHF-UHFFFAOYSA-N
Pubchem ID :	46318122

Safety of [ 1083168-84-6 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301
Precautionary Statements:	P301+P310
Class:	6.1
UN#:	2811
Packing Group:	Ⅲ

Application In Synthesis of [ 1083168-84-6 ]

* 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 [ 1083168-84-6 ]

[ 1083168-84-6 ] Synthesis Path-Downstream 1~9

1
[ 717843-56-6 ]
[ 73183-34-3 ]
[ 1083168-84-6 ]

Yield	Reaction Conditions	Operation in experiment
67%	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 80.0℃;	Step b: 2-Methoxy-5-methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyridine; 3-Bromo-2-methoxy-5-methylpyridine (540 mg, 2.7 mmol), 4,4,4',4',5,5,5',5'- octamethyl-2,2'-bi(l,3,2-dioxaborolane) (810 mg, 3.2 mmol), and Pd(dppf)Cl2 (110 mg, 0.13 mmol) were added to a dry flask and placed under N2. Potassium acetate (800 mg, 8.1 mmol) was weighed directly into the flask. The flask was then evacuated and back filled with N2. Anhydrous N,N-dimethylformamide (DMF) (15 mL) was added and the reaction was heated at 80 0C in an oil bath overnight. The reaction mixture was evaporated to dryness. The residue was dissolved in ethyl acetate (20 mL) and washed with water (20 mL). The organics were dried over sodium sulfate and evaporated to dryness. The resulting material was purified by silica gel chromatography eluting with 0-100% ethyl acetate in hexane to yield 2-methoxy-5- methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (450 mg, 67%). ESI-MS m/z calc. 249.1, found 168.3 (MW-C6H1O+1)+. Retention time 0.27 minutes. 1H νMR (400 MHz, CDCl3) δ 8.03 (m, IH), 7.80 (m, IH), 3.94 (s, 3H), 2.22 (s, 3H), 1.36 (s, 12H).

References: [1]Patent: WO2008/141119,2008,A2 .Location in patent: Page/Page column 96.

2
[ 936727-68-3 ]
[ 1083168-84-6 ]
[ 1083167-56-9 ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 120.0℃; for 0.333333h;microwave irradiation;Product distribution / selectivity;	AQ. l-(2.2-Difluorobenzordiϖ.31dioxol-5-yl)-N-(5-methyl-6-(5-methyl-2-oxo-1.2-dihvdropyridin-3-yl)pyridin-2-yl)cvclopropanecarboxamide; Step a: l-(2,2-Difluorobenzo[d][l,3]dioxol-5-yl)-N-(2'-methoxy-3,5'-dimethyl-2, 3 '-bipyridin--ytycyclopropanecarboxamide; N-(6-Chloro-5-methylpyridin-2-yl)-l-(2,2-difluorobenzo[d][l,3]dioxol-5-- I l l - <n="113"/>yFjcyclopropanecarboxamide (73 mg, 0.20 mmol) was dissolved in 2 mL of 1,2- dimethoxyethane in a reaction tube. 2-Methoxy-5-methyl-3-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)pyridine (65 mg, 0.26 mmol), 0.2 mL of an aqueous 2 M sodium carbonate solution, and tetrakis(triphenylphosphine)palladium(0) (12 mg, 0.010 mmol) were added and the reaction mixture was heated at 120 0C for 20 minutes under microwave irradiation. The reaction was diluted with ethyl acetate (5 mL) and washed with water (5 mL). The organics were dried over sodium sulfate and evaporated to dryness. The resulting residue was purified by silica gel chromatography eluting with 0-100% ethyl acetate in hexane to yield l-(2,2- difluorobenzo[d][l,3]dioxol-5-yl)-N-(2'-methoxy-3,5'-dimethyl-2,3'-bipyridin-6- yl)cyclopropanecarboxamide (49 mg, 72%). ESI-MS m/z calc. 453.4, found 454.3 (M+l)+. Retention time 2.10 minutes.

References: [1]Patent: WO2008/141119,2008,A2 .Location in patent: Page/Page column 111-112.

3
[ 1083168-84-6 ]
N-(6-chloro-5-methylpyridin-2-yl)-1-(2,3-dihydrobenzofuran-5-yl)cyclopropanecarboxamide [ No CAS ]
[ 1083168-38-0 ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 80.0℃;	CG. l-(2.3-dihvdrobenzofuran-5-yl)-N-(5-methyl-6-(5-methyl-2-oxo-1.2- dihvdropyridin-3-yl)pyridin-2-yl)cvclopropanecarboxamide; Step a: l-(2,3-dihydrobenzofuran-5-yl)-N-(2'-methoxy-3,5'-dimethyl-2,3'- bipyridin-6-yl)cyclopropanecarboxamide; To N-(6-chloro-5-methylpyridin-2-yl)-l-(2,3-dihydrobenzofuran-5- yl)cyclopropanecarboxamide (0.1 g, 0.3 mmol) in 1,2-dimethoxyethane (3 mL) was added 2- methoxy-5-methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (98 mg, 0.4 mmol), tetrakis(triphenylphosphine)palladium (O) (35 mg, 0.03 mmol), and 2 M sodium carbonate (0.45 mL, 0.9 mmol) and the reaction mixture was heated to 80 0C overnight. The reaction was diluted with ethyl acetate (5 mL) and washed with water (5 mL). The aqueous layer was back extracted with ethyl acetate (5 mL). The organics were dried over sodium sulfate and evaporated. The resulting crude material was purified by silica gel chromatography (eluting with 0-30% ethyl acetate in hexanes) to yield the product (95 mg, 76%). ESI-MS m/z calc. 415.48, found 416.1 (M+l)+. Retention time 1.92 minutes.

References: [1]Patent: WO2008/141119,2008,A2 .Location in patent: Page/Page column 154-155.

4
[ 17282-02-9 ]
[ 1083168-84-6 ]