[ CAS No. 5458-84-4 ] {[proInfo.proName]}

Name: 5458-84-4|1-Iodo-2-methoxy-4-nitrobenzene|98%
Brand: Ambeed
SKU: A298668
Price: 5.0 USD
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Quality Control of [ 5458-84-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 5458-84-4 ]

SDS Specification

Alternatived Products of [ 5458-84-4 ]

Product Details of [ 5458-84-4 ]

CAS No. :	5458-84-4	MDL No. :	MFCD00024590
Formula :	C₇H₆INO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RBFWMPRFYROKPI-UHFFFAOYSA-N
M.W :	279.03	Pubchem ID :	230103
Synonyms :

Calculated chemistry of [ 5458-84-4 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	54.47
TPSA :	55.05 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.7
Log Po/w (XLOGP3) :	2.37
Log Po/w (WLOGP) :	2.21
Log Po/w (MLOGP) :	1.53
Log Po/w (SILICOS-IT) :	0.64
Consensus Log Po/w :	1.69

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.3
Solubility :	0.139 mg/ml ; 0.0005 mol/l
Class :	Soluble
Log S (Ali) :	-3.17
Solubility :	0.19 mg/ml ; 0.000681 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.85
Solubility :	0.391 mg/ml ; 0.0014 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.41

Safety of [ 5458-84-4 ]

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 [ 5458-84-4 ]

* 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 [ 5458-84-4 ]
Downstream synthetic route of [ 5458-84-4 ]

[ 5458-84-4 ] Synthesis Path-Upstream 1~6

1
[ 97-52-9 ]
[ 5458-84-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium iodide; camphorsulfonic acid; sodium nitrite In acetic acid at 20℃; for 24 h;	General procedure: Potassium iodide (5.0 mmol) and sodium nitrite (3.0 mmol) was added at room temperature to a solution of aniline (2.5 mmol) and camphorsulfonic acid (3.0 mmol) in acetic acid (30 ml), and the mixture was stirred for 24 h. The evolution of N₂ was immediately observed. The solvent was removed by a rotary evaporator after completion of the reaction (confirmed by β-naphthol test and TLC). The solid was washed with water and extracted with CH₂Cl₂. The resulting solution was dried over anhydrous MgSO₄ and the solvent was removed under reduced pressure. The pure product was then collected by column chromatography using hexane/ dichloromethane as eluting solvents. Physical and ¹H NMR data were identical to those of a commercially available sample of analytical purity.
71%	Stage #1: With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5 h; Stage #2: With potassium iodide In water at 0 - 20℃;	HCl (2.0 mL) was added slowly to a cold (0°C) stirred solution of 2-methoxy-4-nitrobenzenamine (343 mg. 2.04 mmol) and NaNO2 (170 mg, 2.46 mmol) in H2O (5.0 mL). After the addition was completed, the solution was stirred for a further 30 min at 0°C. Then a solution of KI (524 mg, 3.16 mmol) in H2O (2.0 mL) was added slowly at 0°C. The whole was stirred at r.t. overnight and quenched with CHCl3. The organic layer was washed with Na2S2O3 aq., water and brine, dried and concentrated. Column chromatography (n-hexane : AcOEt=5 : 1 to 3 : 1) gave the title compound (404 mg, 1.45 mol, 71percent) as a pale yellow solid. 1H-NMR (500 MHz, CDCl3) δ: 7.96 (1H, d, J=8.2 Hz), 7.62 (1H, d, J=2.8 Hz), 7.59 (1H, dd, J=2.8, 8.2 Hz), 3.99 (3H, s).

Reference： [1] Tetrahedron, 2013, vol. 69, # 16, p. 3511 - 3517
[2] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 10, p. 979 - 988
[3] Journal of Medicinal Chemistry, 2009, vol. 52, # 15, p. 4869 - 4882
[4] Chem. Zentralbl., 1901, vol. 72, # I, p. 739
[5] Privatmitteilung,
[6] Journal of the American Chemical Society, 1935, vol. 57, p. 1592,1594
[7] P. Ch. S., p. 238[8] Chem. Zentralbl., 1901, vol. 72, # II, p. 97
[9] Tetrahedron, 1993, vol. 49, # 15, p. 3053 - 3064
[10] Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 9, p. 1654 - 1658
[11] New Journal of Chemistry, 2016, vol. 40, # 7, p. 6487 - 6497
[12] Chemistry - A European Journal, 2016, vol. 22, # 48, p. 17407 - 17415

2
[ 869373-61-5 ]
[ 624-31-7 ]
[ 5458-84-4 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 9, p. 1654 - 1658

3
[ 869373-72-8 ]
[ 5458-84-4 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 9, p. 1654 - 1658
[2] Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 9, p. 1654 - 1658

4
[ 197243-46-2 ]
[ 5458-84-4 ]

Reference： [1] P. Ch. S., p. 238[2] Chem. Zentralbl., 1901, vol. 72, # II, p. 97

5
[ 121-88-0 ]
[ 5458-84-4 ]

Reference： [1] P. Ch. S., p. 238[2] Chem. Zentralbl., 1901, vol. 72, # II, p. 97

6
[ 5458-84-4 ]
[ 106877-20-7 ]

Reference： [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 5, p. 1914 - 1931
[2] Patent: WO2017/32840, 2017, A1,

[ 5458-84-4 ] Synthesis Path-Downstream 1~87

1
[ 110-89-4 ]
[ 5458-84-4 ]
[ 118450-89-8 ]

Reference： [1]Journal and Proceedings - Royal Society of New South Wales,1937,vol. 71,p. 435,444

2
[ 92-84-2 ]
[ 5458-84-4 ]
10-(2-methoxy-4-nitro-phenyl)-phenothiazine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1944,vol. 66,p. 888,891

3
[ 5458-84-4 ]
[ 5337-09-7 ]
[ 106590-33-4 ]

Reference： [1]Journal of the American Chemical Society,1935,vol. 57,p. 1592,1594

4
[ 5458-84-4 ]
4-iodo-3-methoxy-phenylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With iron; ammonium chloride; In tetrahydrofuran; methanol; water; at 80℃; for 4.5h;	To a mixture of 16g (404 mg, 1.45 mmol) and NH4Cl (130 mg, 2.43 mmol) in MeOH (7.0 mL), THF (7.0 mL) and H2O (3.5 mL) was added Fe powder (443 mg, 7.93 mmol). The whole was stirred at 80C for4.5 h and then the reaction was quenched with AcOEt and H2O. The resulting mixture was filtered through a pad of Celite and the filtrate was extracted with AcOEt three times. The organic layers were combined, washed with water and brine, dried and concentrated. Column chromatography (n-hexane : AcOEt=3 : 1 to 2 : 1) gave the title compound (372 mg, 1.45 mmol, quant.) as a brown paste. 1H-NMR (500 MHz, CDCl3) delta: 7.44 (1H, d, J=8.5 Hz), 6.21 (1H, d, J=2.8 Hz), 6.11 (1H, dd, J=2.8, 8.5 Hz), 3.81 (3H, s), 3.72 (2H, br s). FAB-MS m/z 249 (MH+).
81.23%	With hydrogenchloride; zinc; In methanol; water; at 20℃; for 72h;	Add 1.0 g (3.58 mmol) of <strong>[5458-84-4]1-iodo-2-methoxy-4-nitrobenzene</strong> to a 50 ml two-port bottle and turn on magnetic stirring.Add 15 ml of 95% ethanol at room temperature.Stir for 30min;Adding an appropriate amount of zinc particles to dilute hydrochloric acid for activation;0.8 (12 mmol) of activated zinc particles were sequentially added to the double-mouth bottle.10ml of 20% hydrochloric acid solution,Stirring at room temperature for 72 h;After the reaction,Stop the reaction,The obtained reaction solution was extracted with ethyl acetate.After salt washing, remove the water layer.After the obtained organic phase is distilled under reduced pressure,The dark red solid product, 2-methoxy-4-iodoaniline, 2.18 g was obtained in a yield of 81.23%.
59%	With tin(ll) chloride; In ethanol; at 20℃; for 4h;Cooling with ice;	1-lodo-2-methoxy-4-nitro-benzene (6.01 g, 21.54 mmol) in absolute ethanol (127 mL) was cooled with an ice bath and treated with SnC (18.83 g, 99.31 mmol). The bath was removed and the mixture was stirred at room temperature for 4 h then poured into ice (300 mL), stirred and treated carefully with saturated aqueous sodium bicarbonate (250 mL) (pH 7-8). The solid was filtered with suction and the panel washed thoroughly with EtOAc (500 mL and 4 x 200 mL). The aqueous layer was separated, dried over sodium sulphate and evaporated. Purification of the crude by flash chromatography on silica gel (hexane/EtOAc 1/1) furnished the title compound (3.17 g, 59%).

Reference： [1]Chemical and Pharmaceutical Bulletin,2014,vol. 62,p. 979 - 988
[2]Patent: CN109776331,2019,A .Location in patent: Paragraph 0019; 0020
[3]Patent: WO2013/14039,2013,A1 .Location in patent: Page/Page column 40-41
[4]Journal of the American Chemical Society,1930,vol. 52,p. 1570

5
[ 19099-54-8 ]
[ 5458-84-4 ]
[ 31539-95-4 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1971,vol. 44,p. 266 - 270

6
[ 5458-84-4 ]
[ 31539-92-1 ]
[ 31458-15-8 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1971,vol. 44,p. 266 - 270

7
[ 5458-84-4 ]
[ 31539-90-9 ]
[ 31539-98-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1971,vol. 44,p. 266 - 270

8
[ 5458-84-4 ]
bis(2-methoxy-4-nitrophenyl) telluride [ No CAS ]

Reference： [1]Chemische Berichte,1994,vol. 127,p. 783 - 786

9
[ 5458-84-4 ]
[ 536-74-3 ]
2-methoxy-4-nitro-1-(phenylethynyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 20℃; for 2h;Inert atmosphere; Sealed flask;	To a mixture of triethylamine (60 mL) and tetrahydrofuran (20 mL) were added l-iodo-2- methoxy-4-nitrobenzene (10 g, 35.8 mmol) and bis(triphenylphosphine)palladium (II) chloride (0.503 g, 0.717 mmol). Phenylacetylene (4.48 g, 43.0 mmol) in tetrahydrofuran (10 mL) was added dropwise to the reaction mixture and the mixture was stirred for 5 minutes. Copper iodide (0.068 g, 0.358 mmol) was added, and the reaction mixture was stirred and purged with nitrogen for 10 minutes. The reaction flask was sealed and stirred for 2 hours at room temperature. The reaction mixture was treated with 200 mL of dichloromethane, washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo leaving a solid. The crude solid was recrystallized from absolute ethanol. The solid was collected by filtration and washed with cold ethanol and dried in vacuo to give the title compound as a tan solid (8.87 g, 98%).

Reference： [1]Patent: WO2012/87833,2012,A1 .Location in patent: Page/Page column 126
[2]Journal of Organic Chemistry,2005,vol. 70,p. 10292 - 10296

10
[ 869373-61-5 ]
[ 624-31-7 ]
[ 5458-84-4 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2005,vol. 78,p. 1654 - 1658

11
C₁₈H₁₆N₄O₃S [ No CAS ]
2-(4-iodo-phenyl)-5-methyl-thiophene [ No CAS ]
[ 5458-84-4 ]
[ 97-52-9 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2005,vol. 78,p. 1654 - 1658

12
[ 869893-91-4 ]
[ 5458-84-4 ]
C₁₄H₁₁ClFNO₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1506 - 1508
[2]Journal of Medicinal Chemistry,2009,vol. 52,p. 4869 - 4882

13
[ 5458-84-4 ]
[ 121459-86-7 ]
10-methoxy-8-nitro-5,6-dihydro-4H-benzo[6,7]cyclohepta[1,2-b]thiophene [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 4827 - 4829
[2]Journal of Organic Chemistry,2008,vol. 73,p. 8705 - 8710

14
[ 354-64-3 ]
[ 5458-84-4 ]
[ 453560-64-0 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4351 - 4373

15
[ 2314-97-8 ]
[ 5458-84-4 ]
[ 453560-74-2 ]

Yield	Reaction Conditions	Operation in experiment
	With copper; In pyridine; at 140℃; for 22h;	Cooled 140 mL pyridine in a large sealable vessel to -40 2C.Bubbled in trifluoromethyl iodide from a gas cylinder, whichhad been kept in freezer overnight. After adding ICF3 for20 min, added <strong>[5458-84-4]2-iodo-5-nitroanisole</strong> (24.63 g) and copperpowder (67.25 g). Sealed vessel and stirred vigorously for22 h at 140 2C After cooling to -50 aC, carefully unsealedreaction vessel and poured onto ice and Et20. Repeatedlywashed with Et20 and H20. Allowed the ice - Et20 mixture towarm to RT. Separated layers, washed organic layer with INHC1 (3x) , then brine, dried over Na2S04, filtered andconcentrated in vacuo. Eluted material through silica gelplug (4.5:1 Hex:CH2Cl2) to provide 5-nitro-2-trifluoromethylanisole.
	copper; In pyridine; at -40 - 140℃; for 22.3333h;	Cooled 140 mL pyridine in a large sealable vessel to -40 C. Bubbled in trifluoromethyl iodide from a gas cylinder which had been kept in freezer overnight. After adding ICF3 for 20 min, added <strong>[5458-84-4]2-iodo-5-nitroanisole</strong> (24.63 g) and copper powder (67.25 g). Sealed vessel and stirred vigorously for 22 h at 140 C. After cooling to -50 C., carefully unsealed reaction vessel and poured onto ice and Et2O. Repeatedly washed with Et2O and H2O. Allowed the ice - Et2O mixture to warm to RT. Separated layers, washed organic layer with 1N HCl (3*), then brine, dried over Na2SO4, filtered and concentrated in vacuo. Eluted material through silica gel plug (4.5:1 Hex:CH2Cl2) to provide 5-nitro-2-trifluoromethylanisole.
		Preparation XXXI-5-nitro-2-trifluoromethylanisole Cooled 140 mL pyridine in a large salable vessel to- [40 C.] Bubbled in trifluoromethyl iodide from a gas cylinder which had been kept in freezer overnight. After adding ICF3 for 20 min, added <strong>[5458-84-4]2-iodo-5-nitroanisole</strong> (24.63 g) and copper powder (67.25 g). Sealed vessel and stirred vigorously for 22 h at [140 C.] After cooling [TO-50 C,] carefully unsealed reaction vessel and poured onto ice and [ET20.] Repeatedly washed with [ETZO] and H2O. Allowed the ice -Et2O mixture to warm to RT. Separated layers, washed organic layer with 1 N [HC1] (3x), then brine, dried over [NA2SO4,] filtered and concentrated in vacuo. Eluted material through silica gel plug (4.5 : 1 [HEX : CH2CL2)] to provide 5- nitro-2-trifluoromethylanisole.

Cooled 140 mL pyridine in a large sealable vessel to -40 0C. Bubbled in ICF3 from a gas cylinder which had been kept in freezer overnight. After adding ICF3 for 20 min, added <strong>[5458-84-4]2-iodo-5-nitroanisole</strong> (24.63 g) and copper powder (67.25 g). Sealed vessel and stirred vigorously for 22 h at 140 0C After cooling to -50 0C, carefully unsealed reaction vessel and poured onto ice and Et2O. Repeatedly washed with Et2O and H2O. The ice - Et2O mixture warmed to RT. Separated layers, washed organic layer with IN HCl (3x), then brine, dried over Na2Stheta4, filtered and concentrated in vacuo. Eluted material through silica gel plug (4.5:1 Hex:CH2Cl2) to provide 5-nitro-2-trifluoromethylanisole.

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4351 - 4373
[2]Patent: WO2006/12374,2006,A1 .Location in patent: Page/Page column 140
[3]Patent: US2003/225106,2003,A1 .Location in patent: Page 74-75
[4]Patent: WO2004/5279,2004,A2 .Location in patent: Page 101-102
[5]Patent: WO2007/48070,2007,A2 .Location in patent: Page/Page column 110

16
[ 5458-84-4 ]
[ 453560-63-9 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4351 - 4373

17
[ 5458-84-4 ]
[ 474953-31-6 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4351 - 4373

18
[ 5458-84-4 ]
[ 769961-18-4 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4351 - 4373

19
[ 5458-84-4 ]
[ 952490-83-4 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4351 - 4373

20
[ 5458-84-4 ]
[ 952490-85-6 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4351 - 4373

21
[ 5458-84-4 ]
[ 952490-86-7 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4351 - 4373

22
[ 5458-84-4 ]
[ 952490-88-9 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4351 - 4373

23
[ 5458-84-4 ]
[ 952490-89-0 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4351 - 4373

24
[ 5458-84-4 ]
[ 474941-22-5 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4351 - 4373

25
[ 5458-84-4 ]
[ 769961-28-6 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4351 - 4373

26
[ 5458-84-4 ]
4-{2-[3-(2-dimethylaminoethoxy)-4-trifluoromethylphenylamino]-1H-benzimidazol-5-yloxy}-pyridine-2-carboxylic acid methyl amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4351 - 4373

27
[ 5458-84-4 ]
[ 769961-13-9 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4351 - 4373

28
[ 5458-84-4 ]
[ 769960-90-9 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4351 - 4373

29
[ 5458-84-4 ]
4-{2-[3-(1-methylpyrrolidin-2-ylmethoxy)-4-trifluoromethyl-phenylamino]-1H-benzimidazol-5-yloxy}-pyridine-2-carboxylic acid methyl amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4351 - 4373

30
[ 5458-84-4 ]
[ 769961-25-3 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4351 - 4373

31
[ 5458-84-4 ]
C₁₅H₁₅F₅N₂OS [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4351 - 4373

32
[ 5458-84-4 ]
R-4-{2-[3-(1-methyl-pyrrolidin-2-ylmethoxy)-4-pentafluoroethyl-phenylamino]-1H-benzimidazol-5-yloxy}-pyridine-2-carboxylic acid methylamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4351 - 4373

33
[ 5458-84-4 ]
C₂₉H₂₆F₃N₅O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4351 - 4373

34
[ 5458-84-4 ]
[ 612498-85-8 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4351 - 4373

35
[ 5458-84-4 ]
[ 882535-01-5 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1506 - 1508

36
[ 5458-84-4 ]
[ 882535-03-7 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1506 - 1508

37
[ 5458-84-4 ]
2-[4-(3-chloro-2-fluoro-benzyl)-3-methoxy-phenylamino]-methylene}-malonic acid diethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1506 - 1508

38
[ 5458-84-4 ]
6-(3-Chloro-2-fluorobenzyl)-1-(2-hydroxyethyl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1506 - 1508

39
[ 5458-84-4 ]
6-(3-chloro-2-fluoro-benzyl)-1-(2-hydroxy-ethyl)-7-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1506 - 1508

40
[ 5458-84-4 ]
1-(2-tert-butyldimethylsilyloxyethyl)-6-(3-chloro-2-fluorobenzyl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1506 - 1508

41
C₁₃H₁₁BrN₄O₃ [ No CAS ]
[ 5458-84-4 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2005,vol. 78,p. 1654 - 1658
[2]Bulletin of the Chemical Society of Japan,2005,vol. 78,p. 1654 - 1658

42
C₁₃H₁₁ClN₄O₃ [ No CAS ]
[ 5458-84-4 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2005,vol. 78,p. 1654 - 1658
[2]Bulletin of the Chemical Society of Japan,2005,vol. 78,p. 1654 - 1658

43
C₁₃H₁₁FN₄O₃ [ No CAS ]
[ 5458-84-4 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2005,vol. 78,p. 1654 - 1658
[2]Bulletin of the Chemical Society of Japan,2005,vol. 78,p. 1654 - 1658

44
[ 869373-72-8 ]
[ 5458-84-4 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2005,vol. 78,p. 1654 - 1658
[2]Bulletin of the Chemical Society of Japan,2005,vol. 78,p. 1654 - 1658

45
C₁₇H₁₈N₄O₅ [ No CAS ]
[ 5458-84-4 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2005,vol. 78,p. 1654 - 1658
[2]Bulletin of the Chemical Society of Japan,2005,vol. 78,p. 1654 - 1658

46
C₁₈H₁₆N₄O₃S [ No CAS ]
[ 5458-84-4 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2005,vol. 78,p. 1654 - 1658
[2]Bulletin of the Chemical Society of Japan,2005,vol. 78,p. 1654 - 1658

47
C₂₂H₃₂N₄O₄Si [ No CAS ]
[ 5458-84-4 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2005,vol. 78,p. 1654 - 1658

48
C₂₉H₃₀N₄O₄Si [ No CAS ]
[ 5458-84-4 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2005,vol. 78,p. 1654 - 1658

49
C₂₉H₃₀N₄O₄Si [ No CAS ]
[ 5458-84-4 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2005,vol. 78,p. 1654 - 1658

50
[ 5458-84-4 ]
[ 733729-21-0 ]

Reference： [1]Journal and Proceedings - Royal Society of New South Wales,1938,vol. 71,p. 435,439

51
[ 5458-84-4 ]
formic acid-(3-methoxy-4-phenoxy-anilide) [ No CAS ]

Reference： [1]Journal and Proceedings - Royal Society of New South Wales,1938,vol. 71,p. 435,439

52
[ 5458-84-4 ]
[ 857620-62-3 ]

Reference： [1]Journal and Proceedings - Royal Society of New South Wales,1938,vol. 71,p. 435,439

53
[ 5458-84-4 ]
[ 857590-98-8 ]

Reference： [1]Journal and Proceedings - Royal Society of New South Wales,1938,vol. 71,p. 435,439

54
[ 5458-84-4 ]
[ 857620-64-5 ]

Reference： [1]Journal and Proceedings - Royal Society of New South Wales,1938,vol. 71,p. 435,439

55
[ 121-88-0 ]
[ 5458-84-4 ]

Reference： [1],,p. 238
Chemisches Zentralblatt,1901,vol. 72,p. 97

56
[ 5458-84-4 ]
[ 232269-64-6 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1942,vol. 17,p. 10,20

57
[ 5458-84-4 ]
4.4'-dinitro-2-hydroxy-2-methoxy-biphenyl [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1942,vol. 17,p. 10,20

58
[ 5458-84-4 ]
(4.4'-dinitro-2'-methoxy-biphenylyl-⁽²⁾)-acetate [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1942,vol. 17,p. 10,20

59
[ 5458-84-4 ]
[ 859931-27-4 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1942,vol. 17,p. 10,20

60
[ 5458-84-4 ]
[ 453560-74-2 ]

Yield	Reaction Conditions	Operation in experiment
		Pyridine (140 mL) was cooled in a large salable vessel TO-40 C. Trifluoromethyl iodide was bubbled in for 20 min from a gas cylinder which had been kept in freezer overnight. 2-Iodo-5-nitroanisole (24.63 g, 88.2 mmol) and copper powder (67.25 g, 1.06 mol) were added. The vessel was sealed and the reaction was stirred vigorously for 22 h at 140 C. The reaction was cooled TO-50 C, and the vessel was carefully opened and poured onto ice and ET2O. After washing with water and ET20, the reaction was warmed to RT. The layers were separated, the organic layer was washed 3x with 1 N HC1 and then brine, dried over NA2SO4, filtered, and concentrated in vacuo. The crude was purified on a short silica gel column (4.5 : 1 HEXANES : CH2CL2) to provide the title compound.

Reference： [1]Patent: WO2004/85425,2004,A1 .Location in patent: Page 98-99

61
[ 7223-42-9 ]
[ 5458-84-4 ]
[ 892870-61-0 ]

Yield	Reaction Conditions	Operation in experiment
51%	With triethylamine;copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); In acetonitrile; at 20℃; for 3h;	Dissolve l-iodo-2-methoxy-4-nitro-benzene (618 mg, 2.21 mmol) in acetonitrile (10 mL) and treat sequentially with l-prop-2-ynyl-pyrrolidine (352 mg, 3.22 mmol), Et3N (2 mL), CuI (77 mg, 0.404 mmol) and Pd(PPh3)4 (360 mg, 0.311 mmol). Stir the mixture at room temperature for 3 h, then dilute with EtOAc (50 mL) and wash with saturated NaHCO3 (30 mL). Dry, filter and concentrate the organic solution. Purify the crude material by flash chromatography, using a linear gradient of 50% EtOAc/hexanes to 100% EtOAc, to give the title compound as an orange oil (292 mg, 51%). MS (ES+) 261.1(M+l)+. 1H NMR (400 MHz, CDCl3) delta: 7.77 (dd, 1H, 7=8.3, 2.2 Hz), 7.70 (d, 1H, 7=2.2 Hz), 7.50 (d, 1H, 7=8.3 Hz), 3.95 (s, 3H), 3.72 (s, 2H), 2.75-2.70 (m, 4H), 1.87-1.83 (m, 4H).

Reference： [1]Patent: WO2006/66174,2006,A1 .Location in patent: Page/Page column 50

62
[ 5458-84-4 ]
[ 3872-23-9 ]
[ 1124148-89-5 ]

Yield	Reaction Conditions	Operation in experiment
	In 1-methyl-pyrrolidin-2-one; at 150℃; for 1h;	The nitro compound (0.33 g, 0.1.2 mmol) and CuSCF3 (0.38 g, 0.2.3 mmol) were combined in N-methyl pyrrolidinone (1.2 mL) and the mixture was stirred at 150 0C for 1 hour. The mixture was cooled to RT, diluted with 2: 1 wate?saturated NaHCO3 (40 mL), followed by aqueous/EtOAc work-up and silica gel chromatography (diethyl ether: hexanes (1:19)) to afford the titled compound.

Reference： [1]Patent: WO2007/64553,2007,A2 .Location in patent: Page/Page column 79

63
[ 697762-17-7 ]
[ 5458-84-4 ]
C₁₄H₁₁Cl₂NO₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 4869 - 4882

64
[ 5458-84-4 ]
[ 5188-07-8 ]
[ 4163-77-3 ]

Yield	Reaction Conditions	Operation in experiment
68.3%	With N-ethyl-N,N-diisopropylamine;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In tetrahydrofuran;Reflux;	Step 1 2-Methoxy-1-methylsulfanyl-4-nitro-benzene 2-Iodo-5-nitroanisole (5.58 g, 20.0 mmol), Pd2(dba)3 (0.025 eq, 457 mg), Xantphos (0.05 eq, 578 mg), Hunigs Base (1 eq, 3.48 ml) and sodium methanethiolate (1 eq, 1.40 g) were dissolved in THF. The mixture was heated to reflux overnight. Upon cooling the mixture was filtered through celite. The filtrate was concentrated in vacuo. The residue was purified by flash chromatography (4:1 Hexanes/Ethyl Acetate) to give 2-methoxy-1-methylsulfanyl-4-nitro-benzene (2.72 g, 68.3%) as a yellow crystalline solid.
30%	With tris-(dibenzylideneacetone)dipalladium(0); triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In tetrahydrofuran;Inert atmosphere; Reflux;	A mixture of <strong>[5458-84-4]1-iodo-2-methoxy-4-nitrobenzene</strong> (1.9 g, 6.8 mmol), NaSMe (500 mg, 7.1 mmol), Pd2(dba)3 (156 mg), Xantphos (197 mg) and TEA (1.18 mL, 8.51 mmol) in THF (20 mL) was purged with argon and heated to reflux overnight. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column (petroleum ether/ethyl acetate, 2:1, v/v) to give (2-methoxy-4- nitrophenyl)(methyl)sulfane as a yellow solid (400 mg, 30%).?H NMR (400 MHz, CDC13): 7.89 (dd, J = 8.8 Hz, 2.4 Hz, 1H), 7.66 (d, J = 2.4 Hz, 1H), 7.15 (d, J= 8.8 Hz, 1H), 4.00 (s, 3H), 2.51 (s, 3H).

Reference： [1]Patent: US2010/160388,2010,A1 .Location in patent: Page/Page column 64
[2]Patent: WO2016/187667,2016,A1 .Location in patent: Page/Page column 125

65
[ 1514-87-0 ]
[ 5458-84-4 ]
[ 453560-74-2 ]

Yield	Reaction Conditions	Operation in experiment
51.1%	With potassium fluoride; copper(l) iodide; In N,N-dimethyl-formamide; at 120℃;	Step 1 2-Methoxy-4-nitro-1-trifluoromethyl-benzene Following the procedure reported in JACS 2003, 125, 12502, <strong>[5458-84-4]2-iodo-5-nitroanisole</strong> (2.79 g, 10.0 mmol), copper(I) iodide (2.2 eq, 4.19 g), and potassium fluoride (2.2 eq, 1.28 g) were dissolved in DMF. ClF2CCO2CH3 (4.4 eq, 4.7 ml) was added and the mixture was heated to 120 C. overnight. Upon cooling, the mixture was diluted with water and diethyl ether and filtered through celite. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (gradient 9:1 to 1:1 Hexanes/Ethyl Acetate) to give 2-methoxy-4-nitro-1-trifluoromethyl-benzene (1.13 g, 51.1%) as a yellow oil.

Reference： [1]Patent: US2010/160388,2010,A1 .Location in patent: Page/Page column 64-65

66
[ 3581-87-1 ]
[ 5458-84-4 ]
[ 1172639-65-4 ]

Yield	Reaction Conditions	Operation in experiment
51%	With silver carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium(0); In acetonitrile; at 60℃;Inert atmosphere;	2-Iodo-5-nitroanisole (0.675 g, 2.42 mmol), Ag2CO3 (1.11 g, 4.0 mmol), [1,1 '- Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.073 g, 0.101 mmol) and PPh3 (0.053 g, 0.20 mmol) were thoroughly mixed. 2-Methythiazole (0.2 g, 2.02 mmol) was added followed by CH3CN (10 ml) and the mixture was purged with N2 for 2 min. The r.m. was stirred at 60 0C overnight. After cooling DCM (20 ml) and acetone (10 ml) were added and the suspension was filtered over diatomaceous earth and extensively washed with DCM. The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography over Silica gel (eluent: DCM). The product fractions were collected and the solvent was evaporated under reduced pressure. Yield: 0.257 g of intermediate 35 (51 %).

Reference： [1]Patent: WO2010/89292,2010,A1 .Location in patent: Page/Page column 73

67
[ 5458-84-4 ]
[ 120-83-2 ]
[ 1240613-93-7 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 6287 - 6300

68
[ 3908-55-2 ]
[ 5458-84-4 ]
[ 4163-77-3 ]

Reference： [1]Synthetic Communications,2010,vol. 40,p. 3691 - 3698

69
[ 5458-84-4 ]
[ 81290-20-2 ]
[ 453560-74-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With copper(l) iodide; cesium fluoride; In sulfolane; at 45℃; for 18h;	A mixture of Cu l (6.80 g, 35.84 mmol ), CsF ( 14. 15 g, 93.18 mmol ) l -iodo-2-methoxy- 4-nitrobenzene ( 10 g, 35.84 mmol ) and sulfolane (20 ml ), was stirred rapidly at 45 C. To this mixture was added trimethyl(trifluoromethyl)silane ( 13.25 g, 93. 1 mmol ) dropwise over 4 hours using a syringe pump, and the resulting mixture was stirred at 45C for 1 8 hours. The mixture was diluted with ethyl acetate (500 mL ) and stirred with Celite for 5 min. The reaction mixture was filtered through a pad of Celite, diluted with ethyl acetate ( 500 mL ). The organic layer was washed with 10% NH4OH, 1.0 N HCl, brine, dried over Na2SC>4, filtered, and concentrated to give the crude product.The crude product was purified by chromatography (ethyl acetate/petroleum ether 0/1 to 1/4) to give intermediate 444 (8 g, 91% yield ) as a white solid.
	With cesium fluoride;copper(l) iodide; In sulfolane; at 20 - 45℃;Inert atmosphere;	Example 18; N-{4-[8-(2,4-Dioxo-tetrahydro-pyrimidin-1-yl)-5-methoxy-6-trifluoromethyl-quinolin-3-yl]-phenyl}-methanesulfonamide (I-29); step 1-; A mixture of Cu(I) (10.03 g) and CsF (21.40 g) was finely ground in a mortar while in a glove bag under nitrogen atmosphere to afford a free-flowing powder and transferred to an oven dried 250 mL round bottom flask fitted with a stir bar and septum. The flask was then charged with <strong>[5458-84-4]2-iodo-5-nitroanisole</strong> (15.17 g) and sulfolane (30 mL) and stirred rapidly at 45 C. To the mixture was added dropwise over 4 h using a syringe pump trimethyl(trifluoromethyl)silane (20 mL) and the resulting mixture stirred at RT overnight. The reaction was diluted with EtOAc (500 mL) and stirred in some CELITE 512. The reaction mixture was filtered though a pad of CELITE. The filtrate was diluted to 1 L with EtOAc and washed with 1 L of 10% aqueous NH4OH, 1 L of 1.0M HCl and 500 mL of brine. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The amber residue was diluted with DCM and purified by flash chromatography (770 g Supelco VersaPak SiO2 column) and eluted with a DCM/hexane gradient (0 to 40% DCM) in 10 column volumes to afford 8.61 g of 82b as a yellow crystalline solid.

Reference： [1]Patent: WO2017/32840,2017,A1 .Location in patent: Page/Page column 226
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 1914 - 1931
[3]Patent: US2010/311760,2010,A1 .Location in patent: Page/Page column 42

70
[ 5458-84-4 ]
[ 174669-73-9 ]
[ 1093656-03-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium hydrogencarbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 100℃; for 1h;	2.00 g (7.17 mmol) of <strong>[5458-84-4]2-iodo-5-nitroanisole</strong>, 2.02 g (14.3 mmol) of (2-fluoropyridin-3-yl)boronic acid (A. Bouillon, J.-C. Lancelot, V. Collot, P. R. Bovy, S. Rault, Tetrahedron 2002, 58, 3323-3328.), 1.81 g (21.5 mmol) of sodium hydrogen carbonate and 117 mg (0.14 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride are heated to 100 C. in a degassed mixture of 40 ml of dioxane and 10 ml of water for 1 h. After cooling, the mixture is diluted with water and extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulfate, clarified over activated carbon and concentrated. Purification is effected by chromatography on silica gel (eluent: dichloromethane) to obtain 1.55 g (87% of theory) of the desired product. 1H NMR (400 MHz, DMSO-d6, delta/ppm): 3.32 (d, 1H), 8.02 (ddd, 1H), 7.95 (dd, 1H), 7.92 (d, 1H), 7.64 (d, 1H), 7.49 (ddd, 1H), 4.10 (s, 3H). HPLC (Method 6): Rt=3.61 min. MS (ESIpos, m/z): 249 (M+H)+.

Reference： [1]Patent: US2010/298293,2010,A1 .Location in patent: Page/Page column 30

71
[ 1204677-42-8 ]
[ 5458-84-4 ]
C₂₃H₂₈N₂O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate; In toluene; at 105℃; for 48h;	General procedure: (S)-3-((R)-Hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid t-butyl ester 11a (250 mg, 0.9 mmol), copper(I) iodide (51 mg, 270 mumol), 1,10-phenanthroline (97 mg, 540 mumol) and 2,4-difluoro-1-iodobenzene (216 muL, 1.8 mmol) were combined in a vial under air. Toluene (1.4 mL, 14 mmol) was added, followed by the addition of cesium carbonate (587 mg, 1.8 mmol). Air was bubbled through the mixture, the vial was sealed, and the mixture was heated at 105C for 48 hours. The mixture was filtered through Celite. The Celite was then rinsed with DCM (2 x 15 ml), and the resultant filtrate was concentrated. The resultant oil was treated with 1.25 M of HCl in EtOH (5.8 mL, 7.2 mmol) and stirred overnight. The mixture was concentrated and purified by reverse phase preparative HPLC (10 to 70% CH3CN in water with 0.5% TFA) to yield 76 mg (97% purity, 26% yield) of the title compound as the mono-TFA salt.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1456 - 1461

72
[ 5458-84-4 ]
[ 1421580-87-1 ]

Reference： [1]Patent: WO2013/14039,2013,A1

73
[ 5458-84-4 ]
[ 1421580-86-0 ]

Reference： [1]Patent: WO2013/14039,2013,A1

74
[ 5458-84-4 ]
[ 1257832-39-5 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 1914 - 1931

75
[ 5458-84-4 ]
[ 106877-20-7 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 1914 - 1931
[2]Patent: WO2017/32840,2017,A1

76
[ 5458-84-4 ]
[ 694514-19-7 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 1914 - 1931

77
[ 5458-84-4 ]
[ 1257832-31-7 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 1914 - 1931

78
[ 5458-84-4 ]
[ 1257832-33-9 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 1914 - 1931

79
[ 5458-84-4 ]
[ 1485749-11-8 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 1914 - 1931

80
[ 5458-84-4 ]
[ 1485749-14-1 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 1914 - 1931

81
[ 5458-84-4 ]
[2-(biphenyl-4-yl)-1,1,2,2-tetrafluoroethyl](trimethyl)silane [ No CAS ]
4-(1,1,2,2-tetrafluoroethyl)-1,1'-biphenyl [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 3466 - 3469

82
[ 5458-84-4 ]
[2-(biphenyl-4-yl)-1,1,2,2-tetrafluoroethyl](trimethyl)silane [ No CAS ]
[ 6999-04-8 ]
4-(1,1,2,2-tetrafluoro-2-iodoethyl)biphenyl [ No CAS ]
C₂₁H₁₅F₄NO₃ [ No CAS ]
4-(1,1,2,2-tetrafluoroethyl)-1,1'-biphenyl [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 3466 - 3469
[2]Organic Letters,2015,vol. 17,p. 3466 - 3469

83
[ 5458-84-4 ]
[2-(biphenyl-4-yl)-1,1,2,2-tetrafluoroethyl](trimethyl)silane [ No CAS ]
C₂₁H₁₅F₄NO₃ [ No CAS ]
4-(1,1,2,2-tetrafluoroethyl)-1,1'-biphenyl [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 3466 - 3469

84
[ 5458-84-4 ]
[2-(biphenyl-4-yl)-1,1,2,2-tetrafluoroethyl](trimethyl)silane [ No CAS ]
C₂₁H₁₅F₄NO₃ [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 3466 - 3469

85
[ 5458-84-4 ]
[ 124898-13-1 ]
[ 453560-64-0 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 3466 - 3469

86
[ 5458-84-4 ]
[ 375853-82-0 ]
[ 1232784-31-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; at 120℃; for 0.333333h;Microwave irradiation; Inert atmosphere;	A suspension of <strong>[5458-84-4]1-iodo-2-methoxy-4-nitrobenzene</strong> (600 mg,2.150 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl) -5, 6-dihydropyridine-1 (2H) -carboxylate(997 mg, 3.23 mmol) and 2M sodium carbonate solution(3225 fll, 6.45 mmol) in 1,4-dioxane (6477 fll) wasdegassed by bubbling nitrogen for 10 minutes followed by the addition of PdC12(dppf)-dichloromethane adduct (88 mg, 0.108 mmol) . The reaction mixture was heated to 120 C under microwave irradiation for 20 minutes. The reaction mixture was diluted with water (20 mL) and extracted intoethyl acetate (3 x 12 mL) . The combined organic phases were dried over Na2504, filtered and concentrated to dryness under reduced pressure. The residue was purified by chromatography (silica 50g cartridge, cyclohexane:ethyl acetate, gradient elution from 95:5 to70:30) to give the title compound as a yellow oil that solidified upon standing (661 mg, 92%) . ?H NMR (300 MHz, CDC13): 3 7.82 (dd, 1H), 7.71 (d, 1H), 7.28 (d, 1H), 5.87 (br s, 1H), 4.07 (q, 2H), 3.91 (s, 3H), 3.60 (t, 2H), 2.48 (br s, 2H), 1.49 (s, 9H). LCMS (Method C): RT = 1.85mi m/z = 279 [M_tBu+H]+.

Reference： [1]Patent: WO2015/92431,2015,A1 .Location in patent: Page/Page column 343

87
[ 5458-84-4 ]
[ 375853-82-0 ]
4-(4-amino-2-methoxyphenyl)piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Patent: WO2015/92431,2015,A1

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P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 5458-84-4 ] {[proInfo.proName]}

Quality Control of [ 5458-84-4 ]

Related Doc. of [ 5458-84-4 ]

Product Details of [ 5458-84-4 ]

Calculated chemistry of [ 5458-84-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 5458-84-4 ]

Application In Synthesis of [ 5458-84-4 ]

[ 5458-84-4 ] Synthesis Path-Upstream 1~6

[ 5458-84-4 ] Synthesis Path-Downstream 1~87

Related Functional Groups of [ 5458-84-4 ]

Aryls

Ethers

Nitroes

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 5458-84-4 ]