1089281-86-6|5-Bromo-4-methyl-2-nitroanisole| Ambeed

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Quality Control of [ 1089281-86-6 ] Purity: 98% SDS Specification

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Product Details of [ 1089281-86-6 ]

CAS No. :	1089281-86-6
Formula :	C₈H₈BrNO₃
M.W :	246.06
SMILES Code :	COC1=CC(Br)=C(C)C=C1[N+]([O-])=O
MDL No. :	MFCD20482626
InChI Key :	RSQRVVVHNGPSGG-UHFFFAOYSA-N
Pubchem ID :	59441753

Safety of [ 1089281-86-6 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301-H311-H331
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501
Class:	6.1
UN#:	2811
Packing Group:	Ⅲ

Application In Synthesis of [ 1089281-86-6 ]

* 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 [ 1089281-86-6 ]

[ 1089281-86-6 ] Synthesis Path-Downstream 1~15

1
[ 106579-00-4 ]
[ 1089281-86-6 ]

Yield	Reaction Conditions	Operation in experiment
77%	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 20℃; for 3.5h;	Intermediate B101 : 5-methyl-2-(methyloxy)-4-{4-[2-(methylsulfonyl)ethyl]-1- piperazinyljaniline; Step A/Intermediate B102: 1-bromo-2-methyl-5-(methyloxy)-4-nitrobenzene; To 2-methyl-5-(methyloxy)-4-nitroaniline (18.3 g, 100.45 mmol) in 200 mL of acetonitrile was added t-butylnitrite (23.8 g, 231 mmol). To the stirring solution was added copper (II) bromide (53.85 g, 241 mmol) over 30 minutes. The mixture was stirred for 3 hour. The acetonitrile was rotovaped down. The crude product was <n="140"/>partitioned between ether and 1 N HCI (aq). The ether layer was washed several times with 1 N HCI (aq), dried (Na2SO4), filtered, and rotovaped down. The crude product was taken up as a suspension in 1 :10 ether/hexanes and filtered. The solids were washed with 1 :10 ether/hexanes, and dried under vacuum to give 1-bromo-2- methyl-5-(methyloxy)-4-nitrobenzene (19 g, 77.22 mmol, 77%) as a yellow solid. 1H NMR (400 MHz, CDCI3) δ ppm 7.75 (s, 1 H), 7.26 (s, 1 H), 3.93 (s, 3 H), 2.37 (s, 3 H).

References: [1]Patent: WO2009/20990,2009,A1 .Location in patent: Page/Page column 137-138.

2
[ 1089281-86-6 ]
[ 57260-71-6 ]
[ 1116230-00-2 ]

Yield	Reaction Conditions	Operation in experiment
38%	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 60℃; for 24h;	Step B/lntermediate B103: 1 ,1-dimethylethyl 4-[2-methyl-5-(methyloxy)-4- nitrophenyl]-1-piperazinecarboxylate; to a stirred solution of 1-bromo-2-methyl-5-(methyloxy)-4-nitrobenzene (9 g, 36.6 mmol) in 180 ml. of Dioxane was added Pd2(dba)2 (2.14 g, 2.34 mmol), XANTPHOS (2.12 g, 3.65 mmol), cesuim carbonte (50 g, 153.6 mmol) and 1 ,1-dimethylethyl 1- piperazinecarboxylate (13.6g, 73.15 mmol). The resulting slurry was warmed to 6O0C for 24 hours. The dioxane was removed under reduced pressure and the crude mixture was taken up in ether and filtered to remove cesium carbonate. The ether was, washed with water, dried (Na2SO4), filtered, and rotovaped down. The crude product was purified by flash chromatography to give 1 ,1-dimethylethyl 4-[2-methyl-5- (methyloxy)-4-nitrophenyl]-1 -piperazinecarboxylate (4.83 g, 13.75 mmol, 38%). 1H NMR (400 MHz, CDCI3) δ ppm 7.81 (s, 1 H), 6.56 (s, 1 H), 3.92 (s, 3 H), 3.52 - 3.63 (m, 4 H), 2.88 - 2.99 (m, 4 H), 2.25 (s, 3 H), 1.47 (s, 9 H).

References: [1]Patent: WO2009/20990,2009,A1 .Location in patent: Page/Page column 138.

3
[ 1089281-86-6 ]
C₁₃H₁₆N₂O₃ [ No CAS ]

References: [1]Patent: WO2017/125530,2017,A1 .

4
[ 1089281-86-6 ]
C₁₆H₂₂N₂O₄ [ No CAS ]

References: [1]Patent: WO2017/125530,2017,A1 .

5
[ 1089281-86-6 ]
C₁₆H₂₄N₂O₄ [ No CAS ]

References: [1]Patent: WO2017/125530,2017,A1 .

6
[ 1089281-86-6 ]
4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester [ No CAS ]
tert-butyl 4-(5-methoxy-2-methyl-4-nitrophenyl)-3,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%		A solution of 5-bromo-4-methyl-2-nitroanisole (60.00 mg, 0.24 mmol) and N-Boc1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester (202.00 mg, 0.65 mmol) in 1,4-dioxane (5 mL) was degassed by bubbling Ar through the stirred solution in a 10 mL screw-top reaction vial for 10 mm. Freshly prepared 2M aqueous sodium carbonate (0.50 ml, 1.0 mmol), degassed by bubbling N2 through the stirred solution for 15 mm, was added, followed by the catalyst [1,1’- bis(diphenylphosphino)ferrocene] dichloropalladium(II), complex withdichloromethane (20.00 mg, 0.027 mmol). The reaction vial was sealed under Ar and the mixture heated to 100 C (block temperature) for 16 h. The mixture was cooled to rt and diluted with EtOAc (50 mL) and water (25 mL). The aqueous layer was separated and further extracted with EtOAc (25 mL). The combined organic layers were washed with water (25 mL), brine (10 mL), dried over Na2SO4, filtered through a plug ofcelite and evaporated to give a red gum. This residue was purified by column chromatography on silica gel (Si02, 4 g, 50 jim cartridge, mobile phase:cyclohexane/EtOAc, 1CV 100% cyclohexane, then linear gradient from 1:0 to 0:1). The desired fractions were combined and evaporated to give 94 mg of intermediate 316 (quant. yield, red glass).
98%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 100℃; for 16h;Inert atmosphere;	To a solution of <strong>[1089281-86-6]1-bromo-5-methoxy-2-methyl-4-nitrobenzene</strong> (500.0 mg, 2.1 mmol) in 10 mL of dioxane was added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)-3,6-dihydropyridine-1(2H)-carboxylate (826.0 mg, 2.7 mmol), Pd(dppf)2Cl2 (75.0 mg, 0.1 mmol) and Na2CO3 (434.0 mg, 4.1 mmol, 2.0 M in H2O). The resulting mixture was stirred at 100C under N2 for 16 hours. After TLC showed reaction completion, the reaction solution was diluted with aq. Na2CO3 and extracted twice with EtOAc, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE:EA = 3:1) to afford 2: tert-butyl 4-(5-methoxy-2-methyl-4-nitrophenyl)- 3,6-dihydropyridine-1(2H)-carboxylate as a yellow solid (700.0 mg, 98.0%). 1H NMR (400 MHz, DMSO-d6) δ 7.73 (s, 1H), 7.05 (s, 1H), 5.69 (s, 1H), 3.98 (s, 2H), 3.89 (s, 4H), 3.55 (t, J = 5.6 Hz, 3H), 2.36 - 2.29 (m, 6H), 2.21 (s, 4H), 1.44 (s, 9H).

References: [1]Patent: WO2017/125530,2017,A1 .Location in patent: Page/Page column 287.
[2]Patent: WO2021/173677,2021,A1 .Location in patent: Paragraph 00283; 00287.
[3]Patent: WO2022/63106,2022,A1 .Location in patent: Page/Page column 96-97.

7
[ 67-56-1 ]
[ 64695-96-1 ]
[ 1089281-86-6 ]