[ CAS No. 121859-57-2 ] {[proInfo.proName]}

Name: 121859-57-2|5,6-Dichloro-1H-indole|98%
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Quality Control of [ 121859-57-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 121859-57-2 ]

Product Details of [ 121859-57-2 ]

CAS No. :	121859-57-2	MDL No. :	MFCD01075036
Formula :	C₈H₅Cl₂N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ILINOHVVKWYAFM-UHFFFAOYSA-N
M.W :	186.04	Pubchem ID :	10487776
Synonyms :

Calculated chemistry of [ 121859-57-2 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	48.32
TPSA :	15.79 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) :	-5.09 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.91
Log Po/w (XLOGP3) :	3.3
Log Po/w (WLOGP) :	3.47
Log Po/w (MLOGP) :	2.73
Log Po/w (SILICOS-IT) :	3.8
Consensus Log Po/w :	3.04

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.68
Solubility :	0.0391 mg/ml ; 0.00021 mol/l
Class :	Soluble
Log S (Ali) :	-3.31
Solubility :	0.0917 mg/ml ; 0.000493 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.52
Solubility :	0.00567 mg/ml ; 0.0000305 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.29

Safety of [ 121859-57-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 121859-57-2 ]

* 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 [ 121859-57-2 ]
Downstream synthetic route of [ 121859-57-2 ]

[ 121859-57-2 ] Synthesis Path-Upstream 1~5

1
[ 6374-92-1 ]
[ 121859-57-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	With BH₃ In tetrahydrofuran	Preparation 30 5,6-Dichloro-indole This material was produced in 93percent yield from 5,7-dichloro-isatin (1 eq) and BH₃ /THF (6 mol eq.) utilizing a method analogous to that described for 6-chloro-5-fluoro-indole (Preparation 29).

Reference： [1] Patent: US5736534, 1998, A,

2
[ 229481-09-8 ]
[ 121859-57-2 ]

Yield	Reaction Conditions	Operation in experiment
27%	With iron; acetic acid In ethanol at 60 - 90℃; for 3 h;	Iron filings (133 g, 2.39 mmol) were added to a 60 °C solution of (E)-2-(4,5- dichloro-2-nitrophenyl)-N,N-dimethylethenamine (37 g, 120 mmol) and acetic acid (500 mL) in ethanol (500 mL), and the resulting solution stirred for 3 h at 90 °C . The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated, and the residue was diluted with 500 mL of water and extracted with 2x500 mL of ethyl acetate. The combined organic phases were washed with 500 mL of brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with ethyl acetate/petroleum ether (1 : 10)) to afford 5,6-dichloro-lH-indole (6 g, 27percent) as a brown solid. MS: (ESI, m/z): 186[M+H]+.

Reference： [1] Patent: WO2018/75959, 2018, A1, . Location in patent: Paragraph 0643-0644

3
[ 7494-45-3 ]
[ 4637-24-5 ]
[ 121859-57-2 ]

Reference： [1] RSC Advances, 2014, vol. 4, # 9, p. 4672 - 4675
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 10, p. 1598 - 1612

4
[ 95-75-0 ]
[ 121859-57-2 ]

Reference： [1] Patent: WO2018/75959, 2018, A1,

5
[ 7494-45-3 ]
[ 121859-57-2 ]

Reference： [1] Patent: WO2018/75959, 2018, A1,

[ 121859-57-2 ] Synthesis Path-Downstream 1~78

1
[ 7494-45-3 ]
[ 4637-24-5 ]
[ 121859-57-2 ]

Reference： [1]RSC Advances,2014,vol. 4,p. 4672 - 4675
[2]Journal of Medicinal Chemistry,1998,vol. 41,p. 1598 - 1612

2
[ 121859-57-2 ]
[ 162100-53-0 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1598 - 1612

3
[ 121859-57-2 ]
5,6-Dichloro-1-(pyridin-3-ylcarbamoyl)indoline [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1598 - 1612

4
[ 6374-92-1 ]
[ 121859-57-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	With BH3; In tetrahydrofuran;	Preparation 30 5,6-Dichloro-indole This material was produced in 93% yield from 5,7-dichloro-isatin (1 eq) and BH3 /THF (6 mol eq.) utilizing a method analogous to that described for 6-chloro-5-fluoro-indole (Preparation 29).

Reference： [1]Patent: US5736534,1998,A

5
[ 1445-73-4 ]
[ 121859-57-2 ]
5,6-dichloro-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 9 5,6-dichloro-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole Beginning with 0.136 gm (0.88 mMol) <strong>[121859-57-2]5,6-dichloro-1H-indole</strong> and 0.216 mL (1.75 mMol) 1-methyl-4-piperidone, 0.150 gm (61%) of the title compound were recovered as a white solid. m.p.=255-257 C. MS(FD): m/e=280 (M-1) EA: Calculated for: C14 H14 N2 Cl2: Theory: C, 59.80; H, 5.02; N, 9.96. Found: C, 59.65; H, 4.85; N, 9.91.
		EXAMPLE 9 5,6-dichloro-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole Beginning with 0.136 gm (0.88 mMol) <strong>[121859-57-2]5,6-dichloro-1H-indole</strong> and 0.216 mL (1.75 mMol) 1-methyl-4-piperidone, 0.150 gm (61%) of the title compound were recovered as a white solid. m.p.= 255-257C MS(FD): m/e=280 (M-1) EA: Calculated for: C14H14N2Cl2: Theory: C, 59.80; H, 5.02; N, 9.96. Found: C, 59.65; H, 4.85; N, 9.91.

Reference： [1]Patent: US5846982,1998,A
[2]Patent: EP812826,1997,A1

6
[ 121859-57-2 ]
1-(5,6-dichloro-1H-indol-3-yl)-2,2,2-trifluoroethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%		a) 1-(5,6-Dichloro-1H-indol-3-yl)-2,2,2-trifluoro-ethanone; Using a procedure described in J. Med. Chem. 1991, 34, 140, from 0.120 g (0.64 mmol) of <strong>[121859-57-2]5,6-dichloro-1H-indole</strong> were prepared 0.11 g (59%) of the title compound as a white solid.

Reference： [1]Patent: US2007/21463,2007,A1 .Location in patent: Page/Page column 22

7
[ 121859-57-2 ]
[ 1019775-10-0 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 3116 - 3119

8
[ 68-12-2 ]
[ 121859-57-2 ]
[ 1227578-94-0 ]

Yield	Reaction Conditions	Operation in experiment
78.95%		Add 5 mL of N,N-dimethylformamide (DMF) to a 50 mL three-necked flask, cool to below 0 C, and slowly add phosphorus oxychloride (280 uL, 2.96 mmol). After the addition is complete, let stand at room temperature and continue to stir. After 30 minutes,A solution of 25 mL of 6-chloro-1H-indole (II-7, 0.50 g, 2.69 mmol) in DMF was added dropwise under ice-cooling, and the temperature was controlled below 10 C. After the addition was completed, the temperature was raised to 35 C and stirred for 1 h.The reaction was monitored by TLC. After the reaction was completed, the reaction was quenched by adding 10 g of crushed ice under ice cooling, and then 1 mol/L NaOH solution was slowly added thereto to adjust the pH to 8 to 9, and the temperature of the dropping process was not more than 40 C. After the completion of the dropwise addition, the mixture was heated to reflux for 1 h, the stirring was stopped, the mixture was cooled to room temperature, 15 mL of water was added dropwise, and the filter cake was washed with water until neutral.After drying, 0.45 g of a reddish brown solid III-7 was obtained in a yield of 78.95%.

Reference： [1]Patent: CN109942545,2019,A .Location in patent: Paragraph 0244; 0246-0248
[2]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 4783 - 4792

9
[ 50-00-0 ]
[ 210562-49-5 ]
[ 121859-57-2 ]
[ 1266605-89-3 ]

Reference： [1]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 3467 - 3470

10
[ 121859-57-2 ]
[ 98640-00-7 ]

Reference： [1]Patent: US2014/288045,2014,A1
[2]Patent: WO2016/44772,2016,A1

11
[ 121859-57-2 ]
1-(3-(4-(2-(5,6-dichloro-1H-indol-3-yl)acetyl)piperazin-1-yl)azetidin-1-yl)prop-2-en-1-one [ No CAS ]

Reference： [1]Patent: US2014/288045,2014,A1
[2]Patent: WO2016/44772,2016,A1

12
[ 623-73-4 ]
[ 121859-57-2 ]
ethyl 2-(5,6-dichloro-1H-indol-3-yl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8.2%	With copper(II) bis(trifluoromethanesulfonate); In dichloromethane; at 20℃; for 16h;	Example 47 Ethyl 2-(5,6-dichloro-1H-indol-3-yl)acetate To a mixture of <strong>[121859-57-2]5,6-dichloro-1H-indole</strong> (1.0 g, 5.37 mmol), Cu(OTf)2 (194 mg, 0.537 mmol) in DCM (15 mL) at RT, ethyl 2-diazoacetate (918 mg, 8.05 mmol) was added dropwise. The resulting mixture was stirred at RT for 16 h, quenched with water, and then extracted dichloromethane. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by Prep-HPLC to afford the desired product (120 mg, 8.2% yield) as light yellow solid. ESI-MS m/z: 272.1[M+H]+.
8.2%	With copper(II) bis(trifluoromethanesulfonate); In dichloromethane; at 20℃; for 16h;	To a mixture of <strong>[121859-57-2]5,6-dichloro-1H-indole</strong> (1.0 g, 5.37 mmol), Cu(OTf)2 (194 mg, 0.537 mmol) in DCM (15 mL) at RT, ethyl 2-diazoacetate (918 mg, 8.05 mmol) was added dropwise. The resulting mixture was stirred at RT for 16 h, quenched with water, and then extracted dichloromethane. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by Prep-HPLC to afford the desired product (120 mg, 8.2% yield) as light yellow solid. ESI-MS m/z:272.1 [M+H].

Reference： [1]Patent: US2014/288045,2014,A1 .Location in patent: Paragraph 0658
[2]Patent: WO2016/44772,2016,A1 .Location in patent: Paragraph 337; 338

13
[ 121859-57-2 ]
[ 1404532-74-6 ]