[ CAS No. 83004-13-1 ]

Name: 2-Bromo-6-ethylpyridine
Brand: Ambeed
SKU: A323538
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Quality Control of [ 83004-13-1 ]

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COA GC NMR CNMR HPLC/UPLC LC-MS SDS

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SDS

Product Details of [ 83004-13-1 ]

CAS No. :	83004-13-1	MDL No. :	MFCD11869660
Formula :	C₇H₈BrN	Boiling Point :	217.9±20.0°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	186.05	Pubchem ID :	12954800
Synonyms :

Computed Properties of [ 83004-13-1 ]

TPSA :Topological Polar Surface Area	12.9	H-Bond Acceptor Count :	1
XLogP3 :	2.7	H-Bond Donor Count :	0
SP3 :	0.29	Rotatable Bond Count :	1

Safety of [ 83004-13-1 ]

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

Application In Synthesis of [ 83004-13-1 ]

Upstream synthesis route of [ 83004-13-1 ]
Downstream synthetic route of [ 83004-13-1 ]

[ 83004-13-1 ] Synthesis Path-Upstream 1~4

1
[ 5315-25-3 ]
[ 74-88-4 ]
[ 83004-13-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.62 h; Inert atmosphere; Cooling with acetone-dry ice Stage #2: at -78 - 20℃; for 2.50 h; Inert atmosphere; Cooling with acetone-dry ice	Preparation 23 Synthesis of 2-bromo-6-ethyl-pyridine Add under nitrogen a solution of 2.5 M n-butyllithium in hexanes (186.74 mL, 0.467 mol) over 41 min to a solution of diisopropylamine (68.7 mL, 0.488 mol) in tetrahydrofuran (745 mL, 9.16 mol) at -78° C. (dry-ice/acetone bath). Stir for 15 min and add 2-bromo-6-methylpyridine (49.3 mL, 0.424 mol) dropwise over 22 min. Stir 15 min, add methyl iodide (52.87 mL, 0.848 mol) dropwise over 1 hour and then warm to room temperature over 1.5 hour. Add water (250 mL) while cooling with a dry-ice/acetone bath and separate the layers. Extract the aqueous phase twice with ethyl acetate (300 mL). Combine the organic phases, concentrate and purify by silica gel chromatography, gradient eluding from 100:0 to 80:20 using hexanes:ethyl acetate, to give the title compound as a yellow oil (59.74 g, 75percent). ¹H NMR (CDCl₃) δ 1.28 (t, 3H), 2.80 (q, 2H), 7.11 (d, 1H), 7.27 (d, 1H), 7.45 (t, 1H).
46%	Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1.00 h; Stage #2: at 20℃; for 3.00 h;	To a solution of 2-bromo-6-methylpyridine (CAS 5315-25-3) (2.0 g, 11.7 mmol, 1.0 eq) in THF (10 mL) was added LDA (12.3 mL, 12.3 mmol, 1.05 eq) at -78 °C. After stirring at -78 °C for 1 h, CH₃I (1.8 g, 12.3 mmol, 1.05 eq) was added to the mixture. The mixture was stirred at rt for 3 h. The mixture was quenched with sat. NH₄C1 (2 mL), diluted with water (50 mL) and extracted with EA (2 x 100 mL). The combined organic phase was washed with brine and dried over Na₂S0₄. After concentration, the residue was purified by silica gel chromatography with PE/EA (20/1) as eluent to give 2-bromo-6-ethylpyridine. 1.0 g, as a yellow solid, Y: 46percent. ESI-MS (M+H)⁺: 185.9, 187.9.
46%	Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1.00 h; Stage #2: at 20℃; for 3.00 h;	To a solution of 2-bromo-6-methylpyridine (CAS 53 15-25-3) (2.0 g, 11.7 mmol, 1.0 eq) in THF (10 mL) was added LDA (12.3 mL, 12.3 mmol, 1.05 eq) at -78 °C. After stirring at -78°C for 1 h, CH3I (1.8 g, 12.3 mmol, 1.05 eq) was added to the mixture. The mixture was stirred atrt for 3 h. The mixture was quenched with sat. NH4C1 (2 mL), diluted with water (50 mL) and extracted with EA (2 x 100 mL). The combined organic phase was washed with brine and dried over Na2504. After concentration, the residue was purified by silica gel chromatography with PE/EA (20/1) as eluent to give 2-bromo-6-ethylpyridine. 1.0 g, as a yellow solid, Y: 46percent. ESIMS (M+H): 185.9, 187.9.

Reference： [1] Patent: US2009/253750, 2009, A1. Location in patent: Page/Page column 9
[2] Patent: WO2016/11390, 2016, A1. Location in patent: Page/Page column 194
[3] Patent: WO2017/127430, 2017, A1. Location in patent: Page/Page column 52
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 3, p. 501 - 507

2
[ 74-88-4 ]
[ 83004-13-1 ]

Reference： [1] Patent: US2006/211720, 2006, A1. Location in patent: Page/Page column 76

3
[ 109-04-6 ]
[ 74-85-1 ]
[ 83004-13-1 ]

Reference： [1] Journal of the American Chemical Society, 2011, vol. 133, # 45, p. 18086 - 18089

4
[ 21717-29-3 ]
[ 83004-13-1 ]

Reference： [1] Farmaco, Edizione Scientifica, 1982, vol. 37, # 6, p. 398 - 410

[ 83004-13-1 ] Synthesis Path-Downstream 1~10

1
[ 83004-13-1 ]
2-bromo-6-ethyl-4-nitro-pyridine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 829 - 832

2
[ 83004-13-1 ]
[ 83-33-0 ]
3-(6-ethyl-2-pyridyl)indene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%		A solution of 3.0 g (16.1 mmol) of <strong>[83004-13-1]2-bromo-6-ethylpyridine</strong> in25 mL of tetrahydrofuran was added dropwise at 78 C to 6.5 mL (16.1 mmol) of n-BuLi (2.5 M in n-hexane). The resultingreaction mixture was stirred for 45 min at this temperature. Thereafter,2.1 g (16.1 mmol) of 1-indanone dissolved in 25 mL oftetrahydrofuran was added to the stirred solution. After a reactiontime of 2 h between 60 and 78 C, the solution was left at roomtemperature overnight. The reaction was then hydrolyzed with50 mL of saturated ammonium chloride solution. After extractionwith EtOAc (50 mL 3), the combined organic phase was concentrated,and the residue was treated at 0 C with 100 mL of sulfuricacid drop-wisely (85%). The dark red solution was stirred for 2 h atthis temperature and then poured into 150 g of ice water. Theresulting reaction mixture was neutralized with solid sodiumhydroxide and then washed with diethyl ether. Elution withEtOAc/petroleum ether to give 1.60 g (45%) of 3-(6-ethyl-2-pyridyl)indene as a colorless oil. HR-MS (ESI): Calcd for C16H15N +H,222.1283. Found, 222.1282. 1H NMR (400 MHz, CDCl3, ppm): d[8.19 (d, J = 7.6 Hz, 1H), 7.69 (t, J = 8.4 Hz, 1H), 7.54 (t, J = 6.8 Hz,2H), 7.38 (t, J = 7.2 Hz, 1H), 7.29 (t, J = 7.2 Hz, 1H), 7.15 (d,J = 7.6 Hz, 1H), 7.00 (s, 1H) (Py-H, ArH and Cp-H)], 3.57 (s, 2H,Cp-H), 2.96 (q, J = 7.6 Hz, 2H, CH2), 1.43 (t, J = 7.6 Hz, 3H, CH3).13C NMR (100 MHz, CDCl3, ppm): 163.1, 154.4, 144.7, 143.2,136.7, 133.4, 126.2, 124.9, 123.8, 122.3, 120.4, 119.2, 38.3, 31.5,14.0.

Reference： [1]Polyhedron,2019,vol. 158,p. 311 - 315

3
[ 83004-13-1 ]
2-methyl-3-(6-ethyl-2-pyridyl)indene [ No CAS ]

Reference： [1]Polyhedron,2019,vol. 158,p. 311 - 315

4
[ 83004-13-1 ]
2-bromo-3-(6-ethyl-2-pyridyl)indene [ No CAS ]

Reference： [1]Polyhedron,2019,vol. 158,p. 311 - 315

5
[ 32315-10-9 ]
[ 83004-13-1 ]
Bis-(6-ethyl-pyridin-2-yl)-methanone [ No CAS ]
Tris-(6-ethyl-pyridin-2-yl)-methanol [ No CAS ]

Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 8509 - 8512

6
[ 19437-26-4 ]
[ 83004-13-1 ]
(6-Ethyl-pyridin-2-yl)-di-pyridin-2-yl-methanol [ No CAS ]

Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 8509 - 8512

7
[ 83004-13-1 ]
[ 521917-54-4 ]

Reference： [1]Patent: US2003/119870,2003,A1
[2]Patent: US2003/144525,2003,A1

8
[ 79762-54-2 ]
[ 83004-13-1 ]
6-bromo-2-(6-methylpyridin-2-yl)-2H-indazole [ No CAS ]
6-bromo-1-(6-ethylpyridin-2-yl)-1H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%; 26%		The preparation of 6-bromo-l-(6-ethylpyridin-2-yl)-lH-indazole was the same as that of 6-bromo-l-(6-methylpyridin-2-yl)-lH-indazole. The mixture of 6-bromo-l-(6- ethylpyridin-2-yl)-lH-indazole and 6-bromo-2-(6-ethylpyridin-2-yl)-2H-indazole was purified by pre-TLC (PE/EA = 10/1) to give 41-02-0002 and 6-bromo-2-(6-ethylpyridin-2- yl)-2H-indazole. Rf value of 6-bromo-l-(6-ethylpyridin-2-yl)-lH-indazole is more than that of 6-bromo-2-(6-ethylpyridin-2-yl)-2H-indazole. 6-bromo-l-(6-ethylpyridin-2-yl)-lH-indazole, 230 mg, as a yellow solid, Y: 26percent. ESI-MS (M+H)+: 302.0, 304.0. 6-bromo-2-(6-ethylpyridin-2-yl)-2H-indazole, 170 mg, as a yellow solid, Y: 19percent. ESI-MS (M+H)+: 302.0, 304.0.

Reference： [1]Patent: WO2016/11390,2016,A1.Location in patent: Page/Page column 195

9
[ 544-92-3 ]
[ 83004-13-1 ]
[ 59146-66-6 ]

Reference： [1]Farmaco, Edizione Scientifica,1982,vol. 37,p. 398 - 410

10
[ 21717-29-3 ]
[ 83004-13-1 ]

Reference： [1]Farmaco, Edizione Scientifica,1982,vol. 37,p. 398 - 410

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Related Functional Groups of
[ 83004-13-1 ]

Bromides

[ 1037223-35-0 ]

2-Bromo-6-isopropylpyridine

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Related Parent Nucleus of
[ 83004-13-1 ]

Pyridines

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2-Bromo-6-isopropylpyridine

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[ 195044-14-5 ]

2-Bromo-6-tert-butylpyridine

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2-Bromo-4,6-dimethylpyridine

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2-Bromo-6-methylpyridine

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[ CAS No. 83004-13-1 ]

Quality Control of [ 83004-13-1 ]

Related Doc. of [ 83004-13-1 ]

Product Details of [ 83004-13-1 ]

Computed Properties of [ 83004-13-1 ]

Safety of [ 83004-13-1 ]

Application In Synthesis of [ 83004-13-1 ]

[ 83004-13-1 ] Synthesis Path-Upstream 1~4

[ 83004-13-1 ] Synthesis Path-Downstream 1~10

Related Functional Groups of [ 83004-13-1 ]

Bromides

Related Parent Nucleus of [ 83004-13-1 ]

Pyridines

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[ 83004-13-1 ]