220185-63-7|4,5-Dichloro-2-iodoaniline| Ambeed

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Quality Control of [ 220185-63-7 ] Purity: 98% SDS Specification

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Product Details of [ 220185-63-7 ]

CAS No. :	220185-63-7
Formula :	C₆H₄Cl₂IN
M.W :	287.91
SMILES Code :	NC1=CC(Cl)=C(Cl)C=C1I
MDL No. :	MFCD28128363
InChI Key :	PLPUEJCYMXSRKW-UHFFFAOYSA-N
Pubchem ID :	10913187

Safety of [ 220185-63-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 220185-63-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	0.0
Num. H-bond donors	1.0
Molar Refractivity	53.58
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.02 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.03
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.15
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.19
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	3.56
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.39
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.06

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.05
Solubility	0.0255 mg/ml ; 0.0000884 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.37
Solubility	0.124 mg/ml ; 0.00043 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-4.21
Solubility	0.0175 mg/ml ; 0.000061 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	Yes
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.82 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	3.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<0.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.05

Application In Synthesis of [ 220185-63-7 ]

* 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 [ 220185-63-7 ]

[ 220185-63-7 ] Synthesis Path-Downstream 1~35

1
[ 220185-63-7 ]
[ 115-19-5 ]
4-(2-amino-4,5-dichloro-phenyl)-2-methyl-but-3-yn-2-ol [ No CAS ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 9347 - 9350.

2
[ 95-76-1 ]
[ 220185-63-7 ]

Yield	Reaction Conditions	Operation in experiment
43%		INTERMEDIATE 20 - PREPARATION of 4,5-dichloro-2-iodoaniline. Iodine monochloride (1.39 mL; 27.77 mmol) was added to a solution of 3,4- dichloroaniline (4.50 g; 27.77 mmol) in acetic acid (15 mL) and the resulting mixture was stirred 30 minutes at room temperature. The solution was concentrated to dryness, neutralized with sodium bicarbonate and extracted with dichloromethane. The combined organic layers were washed with a saturated solution of sodium thiosulphate, dried over magnesium sulphate and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to afford 3.46 g (43%) of 4,5-dichloro-2-iodoaniline as a brown solid.1 H NMR (DMSO-d6) delta 7.73 (s, 1 H); 6.91 (s, 1 H), 5.63 (br s, 2H).
43%		INTERMEDIATE 50 - PREPARATION of 4,5-Dichloro-2-iodoaniline. Iodine monochloride (1.39 ml 27.77 mmol) was added to a solution of 3,4- dichloroaniline (4.50 g; 27.77 mmol) in acetic acid (15 ml_) and the resulting mixture was stirred for 30 minutes at room temperature. The solution was concentrated to dryness, neutralized with sodium bicarbonate and extracted with dichloromethane. The combined organic layers were washed with a saturated solution of sodium thiosulfate, dried and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to afford 3.46 g (43%) of the title compound as a brown solid. 1 H NMR (DMSO-d6) delta 7.73 (s, 1 H); 6.91 (s, 1 H), 5.63 (br s, 2H).
43%	With Iodine monochloride; In acetic acid; at 20℃; for 0.5h;	Iodine monochloride (1.39 mL; 27.77 mmol) was added to a solution of 3,4-dichloroaniline (4.50 g; 27.77 mmol) in acetic acid (15 mL) and the resulting mixture was stirred for 30 minutes at room temperature. The solution was concentrated to dryness, neutralized with sodium bicarbonate and extracted with dichloromethane. The combined organic layers were washed with a saturated solution of sodium thiosulfate, dried and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to afford 3.46 g (43%) of the title compound as a brown solid. [0643] 1H NMR (DMSO-d6) delta 7.73 (s, 1H); 6.91 (s, 1H), 5.63 (br s, 2H).

43%	With Iodine monochloride; In acetic acid; at 20℃; for 0.5h;	Iodine monochloride (1.39 mL; 27.77 mmol) was added to a solution of 3,4-dichloroaniline (4.50 g; 27.77 mmol) in acetic acid (15 mL) and the resulting mixture was stirred 30 minutes at room temperature. The solution was concentrated to dryness, neutralized with sodium bicarbonate and extracted with dichloromethane. The combined organic layers were washed with a saturated solution of sodium thiosulphate, dried over magnesium sulphate and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to afford 3.46 g (43%) of 4,5-dichloro-2-iodoaniline as a brown solid. [0548] 1H NMR (DMSO-d6) delta 7.73 (s, 1H); 6.91 (s, 1H), 5.63 (br s, 2H).
35%	With Iodine monochloride; In acetic acid; for 4.0h;	Example 1 Preparation of 3- (5, 6-DICHLORO-1 H-INDOL-2-YL)-BENZOIC acid a) 2-lodo-3, 4-dichloro-aniline 3, 4-Dichloroaniline (10.00 g, 61.73 MMOL) was dissolved under argon in acetic acid (150 ML). ICI (15 g, 92.6 MMOL) was dissolved in acetic acid (125 mL), and added slowly to the aniline solution over a period of one hour. After three hours, the reaction mixture was filtered, and the solids were washed with a small amount of acetic acid to give tan colored crystals. These crystals were triturated with water and filtered to give cream white solids (6.00 g). Additional solids had formed in the acetic acid filtrate. These were filtered, triturated with water to give cream colored solids, 2.09 g. Both crystalline batches were combined and RECRYSTALLIZED from warm cyclohexane (35 mL) to give white 4, 5-dichloro-2-iodoaniline as crystalline solid, 6.25 g (35%), mp 79.5-80. 5C. TLC: ethyl acetate-hexane 1: 9, single spot. LCMS 288 (M+H). NMR (D6 DMSO), 7.74 (s, 1H), 6.92 (s, 1H), 5.63 (s, 2H).
26.4%	With water; Iodine monochloride; at 20℃; for 1.86667h;	To a stirred solution of 3,4-dichloroaniline (1.944 g, 12.0 mmol) in acetic acid (40 ml) and under argon at ambient temperature was added a solution of iodine monochloride (2.96 g, 18.23 mmol) in acetic acid (25 ml plus 5 ml wash) dropwise over 22 minutes. After stirring for 1.5 h a solid had precipitated which was filtered off and washed with 5% sodium thiosulphate (100 ml). The solid was dissolved in ethyl acetate (100 ml) and washed with saturated sodium carbonate (100 ml) and water (100 ml). The resulting solid was dried over sodium sulphate, filtered and evaporated to give a dark coloured solid (2.69 g). The crude solid was dissolved in EtOAc/hexane (1:1, vol:vol, 6.0 ml) and loaded on a to a silica cartridge (90 g, Biotage) which was eluted as follows: hexane (600 ml), 4% EtOAc in hexane (1 L) and 5% EtOAc in hexane (1 L). The pure fractions were concentrated in vacuo to give the title compound as an off white solid (0.912 g, yield 26.4%). [00260] 1H NMR (400.13 MHz, CDCl3): 7.66 (1H, s, H-3), 6.81 (1H, s, H-6), 4.14 (2H, bs, -NH2). MS (AP+): m/z 288.0 and 290.1 (MH+).
9%Chromat.	With silver hexafluoroantimonate; iodine; In dichloromethane; at 20℃; for 15.0h;	General procedure: The respective silver salt (0.32 g, 1 mmol) and iodine (0.25 g, 1 mmol) were typically added to a stirred solution of the benzene derivative 1a-i (1 mmol) in dichloromethane (3 mL). The reaction mixture was allowed to stir at room temperature for approximately 16 h (see refPreviewPlaceHolderTable 1, refPreviewPlaceHolderTable 2, refPreviewPlaceHolderTable 3, refPreviewPlaceHolderTable 4, refPreviewPlaceHolderTable 5 and refPreviewPlaceHolderTable 6). The reaction mixture was cooled with ice-cold water, quenched with an aqueous solution of sodium metabisulfite (0.2 mL) and, in the case of anilines, 2 M NaOH (0.2 mL). The mixture was filtered through Celite and the residue was washed with dichloromethane (3×3 mL). The combined filtrate was washed with aqueous sodium bicarbonate (3 mL), water (3 mL), and brine (3 mL). The combined organic phases were dried over Na2SO4 and the solvent was removed under reduced pressure. The residue was redissolved in dichloromethane (10 mL) and the percent conversion of the starting material and the yields of the iodination products were determined by GC-MS using diethylene glycol di-n-butyl ether as internal standard. The relative response factor for the respective analyte (RRFA) was calculated from a calibration standard containing known amounts of the internal standard and the respective analytes using the formula RRFA=AIS·MA/(AA·MIS), where AIS is the peak area of the internal standard, AA is the area of an analyte (i.e., starting material or iodination product), MA is the mass of the analyte and MIS is the mass of the internal standard. The mass of the analyte in the reaction mixture was determined as MA=(RRFA·MIS·AA)/AIS. All samples were analyzed at least in duplicate. The iodination products of selected reactions were separated by column chromatography to obtain milligram quantities for their characterization and use as analytical standards. In the case of 3g, the isolated quantities were not sufficient for 13C NMR analysis.

References: [1]Tetrahedron Letters,2004,vol. 45,p. 8569 - 8573.
[2]Journal of Organic Chemistry,2001,vol. 66,p. 4525 - 4542.
[3]Tetrahedron Letters,1998,vol. 39,p. 9347 - 9350.
[4]Patent: WO2012/80220,2012,A1 .Location in patent: Page/Page column 77-78.
[5]Patent: WO2012/80221,2012,A1 .Location in patent: Page/Page column 87.
[6]Patent: US2013/274260,2013,A1 .Location in patent: Paragraph 0642-0643.
[7]Patent: US2013/289033,2013,A1 .Location in patent: Paragraph 0547-0548.
[8]Patent: WO2005/9993,2005,A1 .Location in patent: Page/Page column 18.
[9]Patent: US6787550,2004,B1 .Location in patent: Page column 22.
[10]Organic Letters,2005,vol. 7,p. 2043 - 2046.
[11]Tetrahedron,2011,vol. 67,p. 7461 - 7469.
[12]Patent: US2014/288045,2014,A1 .Location in patent: Paragraph 0586.

3
[ 220185-63-7 ]
[ 355839-49-5 ]
5,6-Dichloro-2-((2R,5S)-3,6-diethoxy-5-isopropyl-2,5-dihydro-pyrazin-2-ylmethyl)-3-triethylsilanyl-1H-indole [ No CAS ]
[ 355839-61-1 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 4525 - 4542.

4
[ 220185-63-7 ]
6,7-dichloro-1,1-dimethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole [ No CAS ]

References: [1]Organic Letters,2005,vol. 7,p. 2043 - 2046.

5
[ 220185-63-7 ]
2-{5,6-dichloro-3-[5,6-dichloro-3-(2-hydroxy-ethyl)-1H-indol-2-yl]-1,1,3-trimethyl-2,3-dihydro-1H-3a-aza-cyclopenta[a]inden-8-yl}-ethanol [ No CAS ]

References: [1]Organic Letters,2005,vol. 7,p. 2043 - 2046.

6
[ 220185-63-7 ]
5,6-dichloro-L-tryptophan [ No CAS ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 8569 - 8573.

7
[ 220185-63-7 ]
[ 808145-73-5 ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 8569 - 8573.

8
[ 220185-63-7 ]
[ 851663-07-5 ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 8569 - 8573.

9
[ 220185-63-7 ]
5,6-dichloro-D-tryptophan [ No CAS ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 4525 - 4542.

10
[ 220185-63-7 ]
[ 355839-86-0 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 4525 - 4542.

11
[ 220185-63-7 ]
[ 355839-84-8 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 4525 - 4542.

12
[ 220185-63-7 ]
[ 180867-78-1 ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 9347 - 9350.

13
[ 220185-63-7 ]
[ 201929-00-2 ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 9347 - 9350.

14
[ 220185-63-7 ]
[ 220185-64-8 ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 9347 - 9350.

15
[ 220185-63-7 ]
4,5-Dichloro-2-((E)-4-phenyl-but-3-en-1-ynyl)-phenylamine [ No CAS ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 9347 - 9350.

16
[ 220185-63-7 ]
SB 223706 [ No CAS ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 9347 - 9350.

17
[ 220185-63-7 ]
C₁₆H₂₀BCl₂NO₂ [ No CAS ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 9347 - 9350.

18
[ 220185-63-7 ]
[ 220185-67-1 ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 9347 - 9350.

19
[ 318262-67-8 ]
[ 220185-63-7 ]
4-(2-amino-4,5-dichloro-phenylethynyl)-3-benzyloxybenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92.5%	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; at 0 - 20℃; for 6.0h;	3-Benzyloxy-4-ethynylbenzoic acid, benzyl ester (820 mg, 2.395 mmol) and <strong>[220185-63-7]4,5-dichloro-2-iodoaniline</strong> (710 mg, 2.467 mmol) were placed in a three necked flask and the atmosphere was replaced, under vacuum, with argon using a Firestone valve. The solids were then dissolved in THF (13.0 ml), with stirring, and then triethylamine (20 ml) was added. The mixture was cooled in an ice/water bath and the solution degassed four times as described above. Copper (I) iodide (4 mg, 0.02 mmol) and bis(triphenylphosphine)palladium (II) chloride (27 mg, 0.04 mmol) were quickly added and the solution degassed twice more. The cooling bath was then removed and the solution allowed to slowly warm to ambient temperature. After stirring for 6 h at ambient temperature, TC analysis (25% EtOAc/hexane) indicated that all the starting 3-benzyloxy-4-ethynylbenzoic acid, benzyl ester had been consumed. The solvents were removed by evaporation in vacuo and ethyl acetate (50 ml) and dilute sodium hydrogen carbonate (25 ml) were added. The organic fraction was separated and the aqueous phase was back extracted with ethyl acetate (1×25 ml). The total organic fraction was dried over sodium sulphate, filtered and evaporated to give a pale yellow solid (1.28 g). This solid was dissolved in chloroform (50 ml), silica gel added (Merck 9385, 3.25 g) and the mixture concentrated in vacuo. The crude material, preloaded on silica, was purified by chromatography (Biotage 40 g). The cartridge was eluted with chloroform:hexane (70:30), the pure fractions were pooled and concentrated in vacuo to give the title compound (1.113 g, yield 92.5%) as a pale yellow solid. A sample was recrystallised from toluene:chloroform (45:55), mp=152.5-153.5 C. [00263] 1H NMR (400.13 MHz, CDCl3): 7.71 (2H, m, aromatic), 7.57-7.20 (12H, complex m, aromatics), 6.63 (1H, s, aromatic), 5.38 (2H, s, CH2Ph), 5.15 (2H, s, CH2Ph), 3.94 (2H, s, -NH2). MS (AP+): m/z 502.2 and 502.4 (MH+).

References: [1]Patent: US6787550,2004,B1 .Location in patent: Page column 23.

20
[ 220185-63-7 ]
[ 178742-95-5 ]
[ 835595-12-5 ]

Yield	Reaction Conditions	Operation in experiment
47%	With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 20℃; for 3.5h;	b) 3- (2-Amino-4, 5-dichloro-phenylethynyl)-benzoic acid ethyl ester To a stirring solution of 2-iodo-3, 4-dichloro-aniline (1.2 g, 4.16 MMOL) was added 3-ethynyl-benzoic acid ethyl ester (0.72 g, 4.14 mmol ; LIJIMA, Toru; Endo, YASUYUKI, Tsuji, Motonori; Kawachi, Emico; Kagechika, Hiroyuki; Shudo, Koichi; Chem. Pharm. Bull. 1999, 47 (3), 398-404) in triethylamine (20 mL) and THF (20 mL). To this solution was added copper iodide (7 mg, 0.037 MMOL) and palladium bis (triphenylphosphine) dichloride. The mixture was stirred for 3.5 h at rt. The reaction mixture was concentrated and the crude product was dissolved in EtOAc. The EtOAc solution was washed with saturated, aqueous bicarbonate, H2O, and brine. The EtOAc layer was dried over NA2SO4, filtered, and concentrated. The crude product was subjected to silica gel chromatography (15% EtOAc: Hexane) to afford the title compound, 0.66 g (47%). LCMS 334.2 (M+H).

References: [1]Patent: WO2005/9993,2005,A1 .Location in patent: Page/Page column 18.

21
[ 24424-99-5 ]
[ 220185-63-7 ]
[ 835595-19-2 ]

Yield	Reaction Conditions	Operation in experiment
		Example 14 Preparation of 5 « 6-DICHLORO-2-R4-(1 H-TETRAZOL-5-VL)-PHENYL1-1 H-INDOLE a) [4, 5-DICHLORO-2- (4-CYANO-PHENYLETHYNYL)-PHENYL]-CARBAMIC acid t-butyl ester To a stirring solution of (4, 5-dichloro-2-iodo-phenyl)-carbamic acid t-butyl ester (1.2 g, 0.48 MMOL) (prepared by reacting 2-iodo-3, 4-dichloro-aniline and BOC20) was added 4-ethynyl-benzonitrile (0.16 g, 1.24 MMOL) in triethylamine (0.8 mL) and DMF (16 mL). To this solution was added copper iodide (47 mg, 0.25 MMOL) and palladium bis (triphenylphosphine) dichloride (88 mg, 0.12 MMOL). The mixture was stirred for 3.5 h at rt. The reaction mixture was concentrated and the crude product was dissolved in EtOAc. The EtOAc solution was washed with saturated, aqueous bicarbonate, H2O, and brine. The EtOAc layer was dried over NA2SO4 and filtered. The EtOAc extracts were triturated with CH3CN to afford afford a precipitate. The off-white solids were washed with EtOAc and dried under vacuum to provide the title compound, 0.32 g (67%). LCMS 387.0 (M+H).

References: [1]Patent: WO2005/9993,2005,A1 .Location in patent: Page/Page column 23.

22
[ 95-76-1 ]
[ 835595-11-4 ]
[ 89284-72-0 ]
[ 220185-63-7 ]

Yield	Reaction Conditions	Operation in experiment
8%Chromat.; 8%Chromat.; 77%Chromat.	With iodine; silver sulfate; In dichloromethane; at 20℃; for 17.0h;	General procedure: The respective silver salt (0.32 g, 1 mmol) and iodine (0.25 g, 1 mmol) were typically added to a stirred solution of the benzene derivative 1a-i (1 mmol) in dichloromethane (3 mL). The reaction mixture was allowed to stir at room temperature for approximately 16 h (see refPreviewPlaceHolderTable 1, refPreviewPlaceHolderTable 2, refPreviewPlaceHolderTable 3, refPreviewPlaceHolderTable 4, refPreviewPlaceHolderTable 5 and refPreviewPlaceHolderTable 6). The reaction mixture was cooled with ice-cold water, quenched with an aqueous solution of sodium metabisulfite (0.2 mL) and, in the case of anilines, 2 M NaOH (0.2 mL). The mixture was filtered through Celite and the residue was washed with dichloromethane (3×3 mL). The combined filtrate was washed with aqueous sodium bicarbonate (3 mL), water (3 mL), and brine (3 mL). The combined organic phases were dried over Na2SO4 and the solvent was removed under reduced pressure. The residue was redissolved in dichloromethane (10 mL) and the percent conversion of the starting material and the yields of the iodination products were determined by GC-MS using diethylene glycol di-n-butyl ether as internal standard. The relative response factor for the respective analyte (RRFA) was calculated from a calibration standard containing known amounts of the internal standard and the respective analytes using the formula RRFA=AIS·MA/(AA·MIS), where AIS is the peak area of the internal standard, AA is the area of an analyte (i.e., starting material or iodination product), MA is the mass of the analyte and MIS is the mass of the internal standard. The mass of the analyte in the reaction mixture was determined as MA=(RRFA·MIS·AA)/AIS. All samples were analyzed at least in duplicate. The iodination products of selected reactions were separated by column chromatography to obtain milligram quantities for their characterization and use as analytical standards. In the case of 3g, the isolated quantities were not sufficient for 13C NMR analysis.

References: [1]Tetrahedron,2011,vol. 67,p. 7461 - 7469.

23
[ 220185-63-7 ]
[ 94850-15-4 ]

References: [1]Patent: WO2012/80221,2012,A1 .
[2]Patent: US2013/274260,2013,A1 .

24
[ 220185-63-7 ]
[ 1382991-49-2 ]

References: [1]Patent: WO2012/80221,2012,A1 .
[2]Patent: US2013/274260,2013,A1 .

25
[ 220185-63-7 ]
[ 1382991-50-5 ]

References: [1]Patent: WO2012/80221,2012,A1 .
[2]Patent: US2013/274260,2013,A1 .

26
[ 220185-63-7 ]
[ 160194-29-6 ]
[ 1382991-48-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium carbonate; lithium chloride;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 100℃; for 15.0h;	INTERMEDIATE 51 - PREPARATION of 2-(5,6-Dichloro-2-(triethylsilyl)-1 H-indol-3- yl)ethanol. <strong>[220185-63-7]4,5-Dichloro-2-iodoaniline</strong> (1.50 g; 5.21 mmol), 4-(triethylsilyl)but-3-yn-1-ol (1.65 mL; 7.81 mmol), bis(diphenylphosphino)ferrocene]palladium(ll) chloride (0.212 g; 0.260 mmol), lithium chloride (0.221 g; 5.21 mmol) and sodium carbonate (1.10 g; 10.42 mmol) were suspended in DMF (14 mL) and the mixture was stirred at 100C for 15 hours. The solution was concentrated under reduced pressure and diluted with ethyl acetate. The organic layer was successively washed with brine, sodium thiosulfate, dried and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 20 % ethyl acetate in heptane) to afford 2.0 g (quantitative yield) of the title compound as a brown oil.ESI/APCI(+):344 (M+H); ESI/APCI(-):342 (M-H).
100%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; lithium chloride; In N,N-dimethyl-formamide; at 100℃; for 15.0h;	<strong>[220185-63-7]4,5-Dichloro-2-iodoaniline</strong> (1.50 g; 5.21 mmol), 4-(triethylsilyl)but-3-yn-1-ol (1.65 mL; 7.81 mmol), bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.212 g; 0.260 mmol), lithium chloride (0.221 g; 5.21 mmol) and sodium carbonate (1.10 g; 10.42 mmol) were suspended in DMF (14 mL) and the mixture was stirred at 100 C. for 15 hours. The solution was concentrated under reduced pressure and diluted with ethyl acetate. The organic layer was successively washed with brine, sodium thiosulfate, dried and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to afford 2.0 g (quantitative yield) of the title compound as a brown oil. [0645] ESI/APCI(+): 344 (M+H); ESI/APCI(-): 342 (M-H).

References: [1]Patent: WO2012/80221,2012,A1 .Location in patent: Page/Page column 88.
[2]Patent: US2013/274260,2013,A1 .Location in patent: Paragraph 0644-0645.

27
[ 220185-63-7 ]
C₁₅H₁₈Cl₂IN₃O₃S [ No CAS ]

References: [1]Patent: WO2013/155223,2013,A1 .

28
[ 220185-63-7 ]
C₁₅H₁₆Cl₂IN₃O₂ [ No CAS ]

References: [1]Patent: WO2013/155223,2013,A1 .

29
[ 220185-63-7 ]
C₈H₆Cl₂INO₂ [ No CAS ]

References: [1]Patent: WO2013/155223,2013,A1 .

30
[ 220185-63-7 ]
C₁₇H₂₂Cl₂IN₃O₃ [ No CAS ]

References: [1]Patent: WO2013/155223,2013,A1 .

31
[ 220185-63-7 ]
C₁₂H₁₄Cl₂IN₃O [ No CAS ]

References: [1]Patent: WO2013/155223,2013,A1 .

32
[ 220185-63-7 ]
[ 105-36-2 ]
C₁₀H₁₀Cl₂INO₂ [ No CAS ]

References: [1]Patent: WO2013/155223,2013,A1 .Location in patent: Paragraph 0522; 0523.

33
[ 220185-63-7 ]
4,5-dichloro-2-ethylbenzenamine [ No CAS ]

References: [1]Patent: US2014/288045,2014,A1 .

34
[ 220185-63-7 ]
ethyl 2-(4,5-dichloro-2-ethylphenylamino)acetate [ No CAS ]

References: [1]Patent: US2014/288045,2014,A1 .

35
[ 220185-63-7 ]
2-(4,5-dichloro-2-ethylphenylamino)acetic acid [ No CAS ]

References: [1]Patent: US2014/288045,2014,A1 .

Historical Records

Technical Information

• Alkyl Halide Occurrence • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Dihalides • Specialized Acylation Reagents-Vilsmeier Reagent • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Ugi Reaction

Related Functional Groups of
[ 220185-63-7 ]

Aryls

A579712 [6828-35-9]

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A102977 [697-90-5]

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A137020 [70237-25-1]

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A141418 [83171-49-7]

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A233249 [835595-11-4]

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Chlorides

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A102977 [697-90-5]

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Amines

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A102977 [697-90-5]

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A233249 [835595-11-4]

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CAS No.: 220185-63-7

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