[ CAS No. 67929-86-6 ] {[proInfo.proName]}

Name: 67929-86-6|Methyl 5-methoxyindole-2-carboxylate|96%
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SKU: A697704
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Quality Control of [ 67929-86-6 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 67929-86-6 ]

CAS No. :	67929-86-6	MDL No. :	MFCD01074509
Formula :	C₁₁H₁₁NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OXXJVMUTSUYQBR-UHFFFAOYSA-N
M.W :	205.21	Pubchem ID :	2728184
Synonyms :

Calculated chemistry of [ 67929-86-6 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.18
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	56.07
TPSA :	51.32 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) :	-5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.23
Log Po/w (XLOGP3) :	2.21
Log Po/w (WLOGP) :	1.96
Log Po/w (MLOGP) :	1.09
Log Po/w (SILICOS-IT) :	2.37
Consensus Log Po/w :	1.97

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.75
Solubility :	0.364 mg/ml ; 0.00178 mol/l
Class :	Soluble
Log S (Ali) :	-2.92
Solubility :	0.245 mg/ml ; 0.0012 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.49
Solubility :	0.0659 mg/ml ; 0.000321 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.65

Safety of [ 67929-86-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280	UN#:	N/A
Hazard Statements:	H302-H317	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 67929-86-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 67929-86-6 ]
Downstream synthetic route of [ 67929-86-6 ]

[ 67929-86-6 ] Synthesis Path-Upstream 1~4

1
[ 67929-86-6 ]
[ 10601-19-1 ]

Reference： [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 25, p. 6270 - 6282

2
[ 67929-86-6 ]
[ 4382-54-1 ]

Reference： [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 25, p. 6270 - 6282
[2] Chemistry - A European Journal, 2012, vol. 18, # 16, p. 4859 - 4865
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 3, p. 950 - 954

3
[ 5429-56-1 ]
[ 62415-74-1 ]
[ 124-41-4 ]
[ 67929-86-6 ]
[ 98081-83-5 ]

Reference： [1] Journal of Organic Chemistry, 2003, vol. 68, # 15, p. 6011 - 6019

4
[ 67929-86-6 ]
[ 21778-81-4 ]

Reference： [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 19, p. 3624 - 3634
[2] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 561 - 577

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Yield	Reaction Conditions	Operation in experiment
72%	With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 5h; Cooling with ice;	4.2. General procedure for the synthesis of indol-2-ylmethanol(12a-12q) General procedure: A solution of indole-2-carboxylate 11 (1 mmol) in THF (10 mL)was added dropwise to a suspension of LiAlH4 (0.8 mmol) in THF(20 mL) under cooling with ice-water. After stirring at rt for 5 h, thereaction mixture was quenched with water, and then was filtratedthrough a Celite pad. The filtrate was extracted with EtOAc. Theorganic layer was washed with brine, dried over Na2SO4, andevaporated in vacuo. The residue was purified by column chromatography using EtOAc-hexane as an eluent to give thealcohol 12.
	With lithium aluminium tetrahydride In tetrahydrofuran for 0.75h; Ambient temperature;

Yield	Reaction Conditions	Operation in experiment
98.7%	With sulfuric acid; for 6h;Reflux;	A mixture of 9.6 g (0.050 mol) of 5-methoxy-lH-indole-2-carboxylic acid and 4.5 mL of concentrated sulfuric acid in 250 mL of methanol was refluxed for 6 h. The reaction mixture was cooled, concentrated in vacuo and 200 mL of water and 200 mL of dichloromethane was added to the residue. The organic layer was separated and the water phase was extracted with 100 mL of dichloromethane. The combined organic layers were washed with water and saturated sodium hydrogencarbonate solution, dried over sodium sulfate, concentrated and dried to yield 10.17 g (98.7 %) of the title compound. Mp: 178-181 C.
98.7%	With sulfuric acid; In methanol; for 6h;Reflux;	a) 5-Methoxy-1H-indole-2-carboxylic acid methyl ester A mixture of 9.6 g (0.050 mol) of <strong>[4382-54-1]5-methoxy-1H-indole-2-carboxylic acid</strong> and 4.5 mL of concentrated sulfuric acid in 250 mL of methanol was refluxed for 6 h. The reaction mixture was cooled, concentrated in vacuo and 200 mL of water and 200 mL of dichloromethane was added to the residue. The organic layer was separated and the water phase was extracted with 100 mL of dichloromethane. The combined organic layers were washed with water and saturated sodium hydrogencarbonate solution, dried over sodium sulfate, concentrated and dried to yield 10.17 g (98.7%) of the title compound. Mp: 178-181 C.
96%	With sulfuric acid; for 4h;Reflux;	A few drops of concentrated sulphuric acid were added to a suspension containing <strong>[4382-54-1]5-methoxyindole-2-carboxylic acid</strong> (1, 2.00 g, 0.01 mol) in absolute methanol (30 mL). The reaction mixture was heated to reflux for 4 h, cooled to room temperature, and the precipitated solid filtered off to give 2.1 g (96%) of MMIC (2) as yellow crystals, m.p. 450e451 K [13].

	With sulfuric acid; for 24h;Reflux;	General Procedure: To an ice-cold solution of indole-2-carboxylic acid (5.0 g) in methanol (60 mL) was added concentrated sulphuric acid (5 mL). The reaction mixture was refluxed for 24 h and concentrated under reduced pressure. To this reaction mixture was added ice-cold water (50 mL) and extracted with EtOAc (3 X 50 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated to afford the pure product.
	With sulfuric acid; for 24h;Cooling with ice; Reflux;	General procedure: To an ice-cold solution of indole-2-carboxylic acid (5.0 g) in methanol (60 mL) was added concentrated sulphuric acid (5 mL).The reaction mixture was refluxed for 24 h and concentrated under reduced pressure. To this reaction mixture was added ice-cold water (50 mL) and extracted with EtOAc (3 × 50 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated to afford analytically pure product (98% yield) which was used for the next step without further purification.
	With thionyl chloride; for 4h;Reflux;	Into a 250-mL round-bottom flask was placed a solution of <strong>[4382-54-1]5-methoxy-1H-indole-2-carboxylic acid</strong> (10 g, 52.31 mmol, 1.00 equiv) in methanol (100 mL), followed by the additionof thionyl chloride (12.5 g, 105.07 mmol, 2.00 equiv) dropwise with stirring. The resulting solution was heated to reflux for 4 h, cooled to room temperature and concentrated under vacuum to afford 11 g (crude) of methyl 5-methoxy-1H-indole-2-carboxylate as a gray solid

Yield	Reaction Conditions	Operation in experiment
99%	With sodium hydroxide Heating;
	With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.5h; Inert atmosphere;
	With sodium hydroxide In tetrahydrofuran; methanol; water

[ CAS No. 67929-86-6 ] {[proInfo.proName]}

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