[ CAS No. 117832-17-4 ] {[proInfo.proName]}

Name: 117832-17-4|2-Iodo-4,5-dimethylaniline|98%
Brand: Ambeed
SKU: A670931
Rating: 97 (22 reviews)

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Quality Control of [ 117832-17-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 117832-17-4 ]

SDS Specification

Alternatived Products of [ 117832-17-4 ]

Product Details of [ 117832-17-4 ]

CAS No. :	117832-17-4	MDL No. :	MFCD07779006
Formula :	C₈H₁₀IN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZAVYUORHSOSKGS-UHFFFAOYSA-N
M.W :	247.08	Pubchem ID :	14040291
Synonyms :

Calculated chemistry of [ 117832-17-4 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	53.5
TPSA :	26.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.1
Log Po/w (XLOGP3) :	2.56
Log Po/w (WLOGP) :	2.5
Log Po/w (MLOGP) :	3.03
Log Po/w (SILICOS-IT) :	2.99
Consensus Log Po/w :	2.63

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.43
Solubility :	0.0921 mg/ml ; 0.000373 mol/l
Class :	Soluble
Log S (Ali) :	-2.75
Solubility :	0.435 mg/ml ; 0.00176 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.77
Solubility :	0.0421 mg/ml ; 0.00017 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.52

Safety of [ 117832-17-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 117832-17-4 ]

* 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.

Downstream synthetic route of [ 117832-17-4 ]

[ 117832-17-4 ] Synthesis Path-Downstream 1~88

1
[ 95-64-7 ]
[ 117832-17-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With 1-butyl-3-methyl-pyridinium dichloroiodate; at 80℃; for 1h;Inert atmosphere;	3,4-Dimethylaniline (0.1 g, 0.82mmol) and l-butyl-3-methylpyridinium dichloroiodate (BMPDCI) (0.344 g, 0.99 mmol) were added in 10 ml one necked round bottomed flask in an inert atmosphere. The reaction mixture was heated at 80 C for lhr. The reaction was monitored by TLC. After the reaction was completed (TLC), ethyl acetate (10ml) was added followed by addition of water (10ml). The entire reaction mixture was extracted with ethyl acetate (3x10ml). The combined ethyl acetate layer was washed with water, brine and dried over anhydrous sodium sulphate. The separated combined organic layers, was evaporated under vacuum, to afford the crude product. This crude product was purified by silica gel column chromatography to afford pure 2-iodo-4,5-dimethylaniline in 0.19 g, (93% yield). 1H NMR (CDCI3 delta/ppm): 7.31 (s, 1H), 6.49 (s, 1H), 3.79 (broad singlet, 2H, NH2), 2.12-2.14 (d, 6H, Ar-CH3).
85%	With iodine; sodium hydrogencarbonate; In methanol; water; at 20℃; for 1h;Inert atmosphere;	[Example 496] Compound dd47 2-Iodo-4,5-dimethylaniline [1071] Iodine (2.06 g, 8.11 mmol) was added in 10 parts to a mixed solution of 3,4-dimethylaniline (893 mg, 7.37 mmol) and sodium bicarbonate (683 mg, 8.14 mmol) in MeOH/ water (7 ml/7 ml), and it was stirred at room temperature for one hour under a nitrogen atmosphere. Followed by addition of water to the reaction mixture and extraction with dichloromethane, the organic layer was then washed with a saturated aqueous solution of sodium thiosulfate and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, followed by concentration under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/hexane) to yield the title compound (1.54 g, 85%) as a brown solid. LCMS: m/z 248 [M+H]+ HPLC retention time: 1.91 min (analysis condition D)
85%	With iodine; sodium hydrogencarbonate; In methanol; water; at 20 - 25℃; for 1h;Inert atmosphere;	Iodine (2.06 g, 8.11 mmol) was added in 10 parts to a mixed solution of 3,4-dimethylaniline (893 mg, 7.37 mmol) and sodium bicarbonate (683 mg, 8.14 mmol) in MeOH/water (7 ml/7 ml), and it was stirred at room temperature for one hour under nitrogen atmosphere. Followed by addition of water to the reaction mixture and extraction with dichloromethane, the organic layer was then washed with a saturated aqueous solution of sodium thiosulfate and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, followed by concentration under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/n-hexane) to yield the title compound (1.54 g, 85%) as a brown solid. LCMS: m/z 248 [M+H]+ HPLC retention time: 1.91 min (analysis condition C)

Reference： [1]Patent: WO2016/113757,2016,A1 .Location in patent: Page/Page column 17
[2]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 600 - 602
[3]Patent: EP2842939,2015,A1 .Location in patent: Paragraph 1071; 1072
[4]Patent: EP2842946,2015,A1 .Location in patent: Paragraph 1343; 1344
[5]Organic Letters,2019,vol. 21,p. 14 - 17
[6]Journal of Organic Chemistry,2001,vol. 66,p. 4525 - 4542
[7]Synthesis,2016,vol. 48,p. 855 - 864

2
[ 117832-17-4 ]
[ 220906-01-4 ]
[ 220906-03-6 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 657 - 660
[2]Journal of Organic Chemistry,2001,vol. 66,p. 4525 - 4542

3
[ 117832-17-4 ]
[ 1066-54-2 ]
[ 887903-00-6 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 3653 - 3655
[2]Synthesis,2016,vol. 48,p. 855 - 864
[3]Organic and Biomolecular Chemistry,2016,vol. 14,p. 5940 - 5944
[4]Organic and Biomolecular Chemistry,2018,vol. 16,p. 6703 - 6707

4
[ 598-25-4 ]
[ 201230-82-2 ]
[ 117832-17-4 ]
2,2,6,7-tetramethyl-3-methylene-2,3-dihydro-1H-quinolin-4-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 3218 - 3222

5
[ 5664-20-0 ]
[ 201230-82-2 ]
[ 117832-17-4 ]
C₁₅H₁₇NOCH₂CH₂ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 3218 - 3222

6
[ 117832-17-4 ]
4,5-dimethyl-2-ethynylaniline [ No CAS ]

7
[ 117832-17-4 ]
2-(4,6,7-trimethyl-2-quinolinyl)-4,5-dimethylphenylamine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 3653 - 3655
[2]Synthesis,2016,vol. 48,p. 855 - 864

8
[ 117832-17-4 ]
5,6-dimethyl-L-tryptophan [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 4525 - 4542
[2]Tetrahedron Letters,1999,vol. 40,p. 657 - 660

9
[ 117832-17-4 ]
[ 355839-72-4 ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 4525 - 4542
[2]Tetrahedron Letters,1999,vol. 40,p. 657 - 660

10
[ 551-93-9 ]
[ 117832-17-4 ]
[ 1018958-39-8 ]
[ 1018958-54-7 ]

Reference： [1]Synlett,2008,p. 448 - 452

11
[ 17852-28-7 ]
[ 117832-17-4 ]
[ 1018958-44-5 ]

Reference： [1]Synlett,2008,p. 448 - 452

12
[ 719-59-5 ]
[ 117832-17-4 ]
[ 1018958-47-8 ]

Reference： [1]Synlett,2008,p. 448 - 452

13
[ 629-05-0 ]
[ 117832-17-4 ]
4,5-dimethyl-2-oct-1-yn-1-ylaniline [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 4160 - 4165

14
[ 536-74-3 ]
[ 117832-17-4 ]
[ 875930-14-6 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 4160 - 4165
[2]European Journal of Organic Chemistry,2014,vol. 2014,p. 1622 - 1629
[3]Chemical Communications,2017,vol. 53,p. 196 - 199

15
[ 99685-96-8 ]
[ 117832-17-4 ]
[ 1157951-25-1 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 4426 - 4428

16
[ 75-15-0 ]
[ 121-44-8 ]
[ 117832-17-4 ]
[ 1189351-11-8 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 4254 - 4257

17
[ 6320-02-1 ]
[ 117832-17-4 ]
C₁₄H₁₄BrNS [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 1291 - 1294

18
[ 75-15-0 ]
[ 2577-90-4 ]
[ 117832-17-4 ]
[ 1269795-88-1 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 1118 - 1121

19
[ 2415-85-2 ]
[ 117832-17-4 ]
[ 1309764-96-2 ]

Reference： [1]Synlett,2011,p. 623 - 626

20
[ 105-45-3 ]
[ 117832-17-4 ]
[ 1225382-78-4 ]

Reference： [1]Synlett,2011,p. 623 - 626

21
[ 117832-17-4 ]
[ 123-54-6 ]
[ 1309764-91-7 ]

Reference： [1]Synlett,2011,p. 623 - 626

22
[ 75-15-0 ]
[ 100-53-8 ]
[ 117832-17-4 ]
[ 1303996-82-8 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 4200 - 4204

23
[ 117832-17-4 ]
C₁₃H₁₇NO₃ [ No CAS ]

Reference： [1]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 3794 - 3796

24
[ 117832-17-4 ]
[ 1280563-43-0 ]

Reference： [1]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 3794 - 3796

25
[ 117832-17-4 ]
[ 1280563-56-5 ]

Reference： [1]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 3794 - 3796

26
[ 117832-17-4 ]
[ 1280563-61-2 ]

Reference： [1]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 3794 - 3796

27
[ 117832-17-4 ]
[ 1280563-73-6 ]

Reference： [1]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 3794 - 3796

28
[ 117832-17-4 ]
[ 173327-56-5 ]
C₂₅H₄₅NO₃Si₂ [ No CAS ]

Reference： [1]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 3794 - 3796

29
[ 22121-86-4 ]
[ 117832-17-4 ]
[ 221674-53-9 ]
C₁₃H₁₅NO₂ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 6902 - 6908

30
[ 117832-17-4 ]
[ 1356126-54-9 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 836 - 839

31
[ 117832-17-4 ]
[ 1356126-67-4 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 836 - 839

32
[ 117832-17-4 ]
[ 1066-54-2 ]
4,5-dimethyl-2-ethynylaniline [ No CAS ]

Reference： [1]Organic Letters,2012,vol. 14,p. 836 - 839

33
[ 14369-81-4 ]
[ 117832-17-4 ]
[ 1378515-90-2 ]

Reference： [1]Synthesis,2012,vol. 44,p. 1037 - 1042

34
[ 613-94-5 ]
[ 117832-17-4 ]
[ 1378819-29-4 ]

Reference： [1]Synlett,2012,vol. 23,p. 903 - 906

35
[ 536-40-3 ]
[ 117832-17-4 ]
[ 1378819-45-4 ]

Reference： [1]Synlett,2012,vol. 23,p. 903 - 906

36
[ 110-89-4 ]
[ 75-15-0 ]
[ 117832-17-4 ]
[ 1269795-70-1 ]

Yield	Reaction Conditions	Operation in experiment
70%	With copper(II) oxide; potassium hydroxide; In dimethyl sulfoxide; at 110℃; for 6h;	General procedure: A mixture of 2-iodoaniline (0.5 mmol), CS2 (0.6 mmol), an amine (0.6 mmol), CuO nanoparticles (0.5 mmol), and KOH (1.5-2 mmol) in DMSO (3 mL) was stirred at 110 C for 6 h. The cooled solution was partitioned between ethyl acetate and water, and the organic layer was washed with water and brine, and then dried over Na2SO4. After removal of the solvent in vacuo, the residue was purified by silica-gel chromatography to give the desired benzothiazole.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 2518 - 2521

37
[ 103-72-0 ]
[ 117832-17-4 ]
[ 1397746-45-0 ]

Yield	Reaction Conditions	Operation in experiment
	at 20℃; for 1h;Inert atmosphere;	General experimental procedure: o-iodoaniline (1.0 mmol) and phenyl isothiocyanate (1.2 mmol) was mixtured and stirred for 1 h at room temperature (Method A), or o-iodoaniline (1.0 mmol) and phenyl isothiocyanate (1.2 equiv) was mixtured and stirred for 1 h at melting point temperature of phenyl isothiocyanate (Method B), or o-halobenzothioureas (1.0 mmol) (Method C), then anhydrous DMSO (5 ml) and base (3.0 mmol) was added, the stirring continued for about 5-10 h at 130 C (TLC monitor). After the reaction was completed, the reaction mixture was cooled to room temperature and ice-water was added, then the mixture was extracted with EtOAc. The combined organic phase was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum and then the residue was purified by column chromatography (eluent: petroleum ether/ethyl acetate (5:1 to 7:1)) on silica gel to provide the desired product.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 4529 - 4531

38
[ 103-72-0 ]
[ 117832-17-4 ]
[ 1368039-81-9 ]

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 4529 - 4531

39
[ 117832-17-4 ]
[ 1985-12-2 ]
[ 1393130-57-8 ]

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 4529 - 4531

40
[ 117832-17-4 ]
[ 1985-12-2 ]
C₁₅H₁₄BrIN₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	for 1h;Inert atmosphere; Heating;	General experimental procedure: o-iodoaniline (1.0 mmol) and phenyl isothiocyanate (1.2 mmol) was mixtured and stirred for 1 h at room temperature (Method A), or o-iodoaniline (1.0 mmol) and phenyl isothiocyanate (1.2 equiv) was mixtured and stirred for 1 h at melting point temperature of phenyl isothiocyanate (Method B), or o-halobenzothioureas (1.0 mmol) (Method C), then anhydrous DMSO (5 ml) and base (3.0 mmol) was added, the stirring continued for about 5-10 h at 130 C (TLC monitor). After the reaction was completed, the reaction mixture was cooled to room temperature and ice-water was added, then the mixture was extracted with EtOAc. The combined organic phase was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum and then the residue was purified by column chromatography (eluent: petroleum ether/ethyl acetate (5:1 to 7:1)) on silica gel to provide the desired product.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 4529 - 4531

41
[ 2495-35-4 ]
[ 117832-17-4 ]
[ 1404530-46-6 ]

Yield	Reaction Conditions	Operation in experiment
		60.8 g of lithium chloride is added to a solution of 15.5 g of [1,4]-benzoquinone in 350 ml of THF, and it is degassed with nitrogen. 3.2 g of palladium acetate and 23.7 g of benzyl acrylate are added and it is degassed with nitrogen for about 30 minutes. Than a solution of 35.1 g of <strong>[117832-17-4]2-iodo-4,5-dimethylaniline</strong> (prepared according to J. Med. Chem. 2001, 44, 3856-3871) in 150 ml of THF is added and it is stirred overnight. It is filtered and the filtrate is evaporated. The solid residue thus obtained is triturated with ether. It is filtered, the filtrate is washed with a solution of NaOH 0.5N and then with water and with brine. It is evaporated and then the solid residue is purified by silica gel chromatography, eluting with a cyclohexane/EtOAc mixture (8/2; v/v). 57.6 g of the expected compound is obtained in the form of a white powder.1H NMR: DMSO-d6 (250 MHz): delta (ppm): 2.14 (3H, s); 2.19 (3H, s); 4.93 (1H, d); 5.18 (2H, s); 7.23 (1H, s); 7.30-7.45 (5H, m); 7.59 (1H, s); 7.72 (1H, dd); 10.05 (1H, d).
	With p-benzoquinone; lithium chloride;palladium diacetate; In tetrahydrofuran;Inert atmosphere;	Preparation 2.65,6-Dimethyl-1 /-/-indole-3-carboxylic acid.(VIII): X = CH; R4 = Me; R5 = Me.Step 1 : 3-[(2-lodo-4,5-dimethylphenyl)amino]benzyl acrylate (XVIII).60.8 g of lithium chloride is added to a solution of 15.5 g of [1 ,4]- benzoquinone in 350 ml of THF, and it is degassed with nitrogen. 3.2 g of palladium acetate and 23.7 g of benzyl acrylate are added and it is degassed with nitrogen for about 30 minutes. Then a solution of 35.1 g of 2-iodo-4,5- dimethylaniline (prepared according to J. Med. Chem 2001 , 44, 3856-3871 ) in 150 ml of THF is added and it is stirred overnight. It is filtered and the filtrate is evaporated. The solid residue thus obtained is triturated with ether. It is filtered, the filtrate is washed with a solution of NaOH 0.5N and then with water and with brine. It is evaporated and then the solid residue is purified by silica gel chromatography, eluting with a cyclohexane/EtOAc mixture (8/2; v/v). 57.6 g of the expected compound is obtained in the form of a white powder.1H NMR: DMSO-de (250 MHz): delta (ppm): 2.14 (3H, s); 2.19 (3H, s); 4.93 (1 H, d); 5.18 (2H, s); 7.23 (1 H, s); 7.30-7.45 (5H, m); 7.59 (1 H, s); 7.72 (1 H, dd); 10.05 (1 H, d).

Reference： [1]Patent: US2012/277205,2012,A1 .Location in patent: Page/Page column 25
[2]Patent: WO2012/146318,2012,A1 .Location in patent: Page/Page column 55

42
[ 117832-17-4 ]
[ 1360945-45-4 ]

Reference： [1]Patent: US2012/277205,2012,A1
[2]Patent: WO2012/146318,2012,A1

43
[ 117832-17-4 ]
[ 1404530-48-8 ]

Reference： [1]Patent: US2012/277205,2012,A1
[2]Patent: WO2012/146318,2012,A1
[3]Journal of Medicinal Chemistry,2014,vol. 57,p. 7293 - 7316

44
2H-isoindole-1-carbaldehyde [ No CAS ]
[ 117832-17-4 ]
2,3-dimethylisoindolo[2,1-a]quinoxaline [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 4895 - 4902

45
C₉H₆ClNO [ No CAS ]
[ 117832-17-4 ]
N-(2-iodo-4,5-dimethylphenyl)-2H-isoindole-1-carboxamide [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 4895 - 4902

46
[ 5703-26-4 ]
[ 117832-17-4 ]
2-(2-fluoro-4-methoxyphenyl)-6,7-dimethylquinoxaline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With copper(l) iodide; sodium azide; potassium carbonate; N,N`-dimethylethylenediamine; In dimethyl sulfoxide; at 80℃; for 20h;Sealed tube;	General procedure: 2-iodoaniline (54.8 mg, 0.25 mmol) 1a, sodium azide (19.5 mg, 0.3mmol) 3, CuI (4.8 mg, 0.025 mmol), K2CO3 (34.5 mg, 0.25 mmol),phenylacetaldehyde (58 muL, 0.5 mmol) 2a, (DMEDA) (3 muL, 0.025mmol) were taken in a round bottom flask equipped with stirrer in 1.0mL of DMSO. The reaction mixture was heated to 80 C for 20 h.After cooling the room temperature, to the reaction mixture wasadded water (2 mL), and extracted with EtOAc (310 mL). Thecombined organic phases were washed with brine (25 mL), driedover anhydrous MgSO4 and concentrated in vacuo. The residue wassubjected to flash column chromatography with petroleum/ethylacetate (20/1) to afford the final product 4aa as light yellow solid

Reference： [1]Synlett,2013,vol. 24,p. 2315 - 2319

47
[ 122-78-1 ]
[ 117832-17-4 ]
[ 71897-07-9 ]

Yield	Reaction Conditions	Operation in experiment
84%	With copper(l) iodide; sodium azide; potassium carbonate; N,N`-dimethylethylenediamine; In dimethyl sulfoxide; at 80℃; for 20h;Sealed tube;	General procedure: 2-iodoaniline (54.8 mg, 0.25 mmol) 1a, sodium azide (19.5 mg, 0.3mmol) 3, CuI (4.8 mg, 0.025 mmol), K2CO3 (34.5 mg, 0.25 mmol),phenylacetaldehyde (58 muL, 0.5 mmol) 2a, (DMEDA) (3 muL, 0.025mmol) were taken in a round bottom flask equipped with stirrer in 1.0mL of DMSO. The reaction mixture was heated to 80 C for 20 h.After cooling the room temperature, to the reaction mixture wasadded water (2 mL), and extracted with EtOAc (310 mL). Thecombined organic phases were washed with brine (25 mL), driedover anhydrous MgSO4 and concentrated in vacuo. The residue wassubjected to flash column chromatography with petroleum/ethylacetate (20/1) to afford the final product 4aa as light yellow solid

Reference： [1]Synlett,2013,vol. 24,p. 2315 - 2319

48
[ 117832-17-4 ]
[ 1388136-12-6 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 1622 - 1629

49
[ 117832-17-4 ]
[ 1606994-79-9 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 1622 - 1629
[2]European Journal of Organic Chemistry,2014,vol. 2014,p. 1622 - 1629

50
[ 2495-35-4 ]
[ 117832-17-4 ]
3-[(2-iodo-4,5-dimethylphenyl)amino]benzyl acrylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 7293 - 7316

51
[ 117832-17-4 ]
[ 1404532-72-4 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 7293 - 7316

52
[ 117832-17-4 ]
[ 1404529-46-9 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 7293 - 7316

53
[ 117832-17-4 ]
[ 1404535-55-2 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 7293 - 7316

54
[ 117832-17-4 ]
[ 1404535-61-0 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 7293 - 7316

55
[ 117832-17-4 ]
[ 1404532-13-3 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 7293 - 7316

56
[ 117832-17-4 ]
1-methoxycarbonylmethyl-5,6-dimethyl-1H-indole-3-carboxylic acid benzyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 7293 - 7316

57
[ 117832-17-4 ]
2-iodo-4,5-dimethylbenzonitrile [ No CAS ]

Reference： [1]Patent: EP2842939,2015,A1
[2]Patent: EP2842946,2015,A1

58
[ 68-12-2 ]
[ 117832-17-4 ]
[ 1432726-52-7 ]

Yield	Reaction Conditions	Operation in experiment
92%		General procedure: To a two-necked round-bottomed flask fitted with a guard tube, PBr3 (2.7mmol, 0.26 mL), DMF (3 mmol, 0.23 mL) and chloroform (0.80 mL) were added, allowed to cool to 0 C and stirred for 0.5 h. After formation of colourless solid complex, 2-Iodo-4-methyl-phenylamine 2b (1 mmol) in chloroform (5 mL) was added and the reaction mixture was allowed to stir at r.t. for another 1-2 h. After completion, the reaction mixture was neutralized by adding saturated NaHCO3 solution and then extracted with DCM (3X 20 mL). Combined organic layer was washed with brine and dried over Na2SO4. The solvent was evaporated under reduced pressure and the crude product was purified through column chromatography using silica gel (60-120 mesh) and petether/EtOAc (5:1) as eluent.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 353 - 355

59
[ 117832-17-4 ]
[ 861002-62-2 ]

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 353 - 355

60
copper(l) cyanide [ No CAS ]
[ 117832-17-4 ]
[ 28568-03-8 ]

Yield	Reaction Conditions	Operation in experiment
88%		[Example 497] Compound dd48 2-Amino-4,5-dimethylbenzonitrile [1073] Copper(I) cyanide (1.24 g, 12.4 mmol) was added to a solution of <strong>[117832-17-4]2-iodo-4,5-dimethylaniline</strong> (Compound dd46, 1.53 g, 6.21 mmol) in DMF (20 ml), and it was stirred at 150 to 160C for 1.5 hours. After the reaction solution was cooled to room temperature, a 10% aqueous ammonia solution (30 ml) and DCM (30 ml) were added, followed by removal of the insoluble matter by filtration through celite, and it was washed with DCM. The organic layer of the filtrate was concentrated under reduced pressure, and the resultant residue was purified by silica gel column chromatography (ethyl acetate/hexane) to yield the title compound (796 mg, 88%) as a brown solid. LCMS: m/z 147 [M+H]+ HPLC retention time: 0.66 min (analysis condition A)
88%	In N,N-dimethyl-formamide; at 150 - 160℃; for 1.5h;	Copper(I) cyanide (1.24 g, 12.4 mmol) was added to a solution of <strong>[117832-17-4]2-iodo-4,5-dimethylaniline</strong> (Compound ff16, 1.53 g, 6.21 mmol) in DMF (20 ml), and it was stirred at 150 to 160C for 1.5 hours. After the reaction solution was cooled to room temperature, a 10% aqueous ammonia solution (30 ml) and DCM (30 ml) were added, followed by removal of the insoluble matter through celite, and it was washed with DCM. The organic layer of the filtrate was concentrated under reduced pressure, and the resultant residue was purified by silica gel column chromatography (ethyl acetate/n-hexane) to yield the title compound (796 mg, 88%) as a brown solid. LCMS: m/z 147 [M+H]+ HPLC retention time: 0.66 min (analysis condition D)

Reference： [1]Patent: EP2842939,2015,A1 .Location in patent: Paragraph 1073; 1074
[2]Patent: EP2842946,2015,A1 .Location in patent: Paragraph 1345; 1346

61
[ 95-64-7 ]
[ 117832-17-4 ]
[ 1585-13-3 ]

Reference： [1]RSC Advances,2015,vol. 5,p. 88311 - 88315

62
[ 117832-17-4 ]
[ 946147-04-2 ]

Reference： [1]Patent: US9281483,2016,B2
[2]Patent: KR2016/30582,2016,A

63
[ 117832-17-4 ]
[ 946147-15-5 ]

Reference： [1]Patent: US9281483,2016,B2
[2]Patent: KR2016/30582,2016,A

64
[ 117832-17-4 ]
3-(2,6-dimethylphenyl)-6,7-dimethylimidazo[1,2-f]phenanthridine [ No CAS ]

Reference： [1]Patent: US9281483,2016,B2
[2]Patent: KR2016/30582,2016,A

65
[ 117832-17-4 ]
[ 946147-19-9 ]

Reference： [1]Patent: US9281483,2016,B2
[2]Patent: KR2016/30582,2016,A

66
[ 117832-17-4 ]
[ 946147-20-2 ]

Reference： [1]Patent: US9281483,2016,B2
[2]Patent: KR2016/30582,2016,A

67
[ 117832-17-4 ]
3-(2,6-diisopropyl-4-bromophenyl)-6,7-dimethylimidazol[1,2-f]phenanthridine [ No CAS ]

Reference： [1]Patent: US9281483,2016,B2

68
[ 117832-17-4 ]
2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile [ No CAS ]
2,3-dimethyl-6-aminophenanthridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14 g	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate monohydrate; In toluene; at 110℃; for 4h;Inert atmosphere;	To a 1 L round flask was added <strong>[117832-17-4]2-iodo-4,5-dimethylanaline</strong> (24.7 g, 100 mmol), 2-cyanophenylboronic acid, pinacol ester (27.5 g, 120 mmol), dichlorobis(triphenylphosphine) palladium(II) (3.51 g, 5 mmol), potassium phosphate tribasic monohydrate (46.0 g, 200 mmol), and 400 mL of toluene. The reaction was heated to reflux and stirred under a nitrogen atmosphere for 4 hours. After cooling, the precipitate formed was filtered and washed with toluene, hexanes and water. Yield was 14 g.
14 g	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate monohydrate; In toluene; at 110℃; for 4h;Inert atmosphere;	1? round flask for <strong>[117832-17-4]2-iodo-4,5-dimethylaniline</strong>, putting them (24.7 g, 100 mmol), 2-cyano-phenylboronic acid pinacol ester (27.5 g, 120 mmol), dichlorobis (triphenylphosphine ) palladium (II) (3.51 g, 5 mmol), was added potassium phosphate monohydrate three basic ( 46.0 g, 200 mmol) and 400ml toluene . The reaction was heated to reflux, stirred for 4 hours under a nitrogen atmosphere. After cooling, the formed precipitate was filtered, washed with toluene, hexane and water. The yield is 14 g .1 ? round flask in the intermediate chloro-acetaldehyde (50% wt in water, 15.7 [0175] g, 100 mmol), sodium carbonate (15.9 g, 150 mmol) and 2-propanol was added to the 300 It was. It was heated under reflux for 2 hours. The solvent was removed and the residue extracted with CH2Cl2 and was further purified by a silica gel column. Yield is 13 g.

Reference： [1]Patent: US9281483,2016,B2 .Location in patent: Page/Page column 84
[2]Patent: KR2016/30582,2016,A .Location in patent: Paragraph 0171; 0172; 0173; 0174

69
[ 117832-17-4 ]
8-fluoro-2,3-dimethylbenzofuro[3,2-c]quinolin-6(5H)-one [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 5940 - 5944

70
[ 117832-17-4 ]
C₁₆H₁₄BrN [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 5940 - 5944

71
[ 117832-17-4 ]
2,3-dimethylbenzofuro[3,2-c]quinolin-6(5H)-one [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 5940 - 5944

72
[ 117832-17-4 ]
C₁₆H₁₃BrFN [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 5940 - 5944

73
[ 117832-17-4 ]
N-[2-(3-hydroxy-prop-1-ynyl)-4,5-dimethyl-phenyl]-4-methyl-benzenesulfonamide [ No CAS ]

Reference： [1]Synthetic Communications,2016,vol. 46,p. 1249 - 1256

74
[ 117832-17-4 ]
6,7-dimethyl-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-quinolin-4-one [ No CAS ]

Reference： [1]Synthetic Communications,2016,vol. 46,p. 1249 - 1256

75
[ 107-19-7 ]
[ 117832-17-4 ]
C₁₁H₁₃NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 0 - 50℃;	General procedure: PdCl2(PPh3)2 (0.1 mmol) and CuI (0.05 mmol) were added to a solution of 2-iodoaniline derivatives (1 mmol) in Et3N (3 mL) at 0C. Then propargyl alcohol (1.05 mmol) was added slowly. The resulting mixture was stirred at 50C until the starting material disappeared completely monitored by TLC. Then water was added to quench the reaction. The reaction mixture was extracted with ethylacetate and the combined organic phases were washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give a residue. Finally the residue was purified through column chromatography on silica gel (200-300 mesh) with hexane/EtOAc as eluent to afford pure 1j or o-anilinopropargyl alcohols with substitution in the phenyl ring. Halogen including sulfonyl chloride and acyl chloride (1.2 mmol) was added slowly to the mixture of o-aniliopropargy alcohol (1 mmol) and dry pyridine (3 mol) in dry CH2Cl2 (3 mL) at 0C. Then the ice-water bath was removed and the resulting mixture was stirred at room temperature until the starting material disappeared completely monitored by TLC. Then 10% HCl was added to quench the reaction. The reaction mixture was extracted with ethyl acetate and the combined organic phases were washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give a residue. Finally the residue was purified through flash chromatography on silica gel (200-300 mesh) with hexane/EtOAc as eluent to afford the targeted compounds 1a-1h.

Reference： [1]Synthetic Communications,2016,vol. 46,p. 1249 - 1256

76
[ 117832-17-4 ]
[ 610-14-0 ]
N-(2-iodo-4,5-dimethylphenyl)-2-nitrobenzamide [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 3201 - 3205

77
[ 117832-17-4 ]
C₂₃H₁₉N [ No CAS ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 196 - 199

78
[ 1293-79-4 ]
[ 117832-17-4 ]
C₁₉H₁₈FeINO [ No CAS ]