[ CAS No. 7598-91-6 ] {[proInfo.proName]}

Name: 7598-91-6|Ethyl 5-hydroxy-2-methyl-1H-indole-3-carboxylate|97%
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SKU: A875543
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COA NMR CNMR HPLC LC-MS

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CAS No. :	7598-91-6	MDL No. :	MFCD00044575
Formula :	C₁₂H₁₃NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BSNHKSUAAMJXBB-UHFFFAOYSA-N
M.W :	219.24	Pubchem ID :	82073
Synonyms :

Calculated chemistry of [ 7598-91-6 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.25
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	61.37
TPSA :	62.32 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) :	-6.0 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.03
Log Po/w (XLOGP3) :	2.31
Log Po/w (WLOGP) :	2.36
Log Po/w (MLOGP) :	1.37
Log Po/w (SILICOS-IT) :	2.71
Consensus Log Po/w :	2.16

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.87
Solubility :	0.294 mg/ml ; 0.00134 mol/l
Class :	Soluble
Log S (Ali) :	-3.26
Solubility :	0.121 mg/ml ; 0.000553 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.58
Solubility :	0.0571 mg/ml ; 0.000261 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.87

Safety of [ 7598-91-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 7598-91-6 ]

* 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 [ 7598-91-6 ]
Downstream synthetic route of [ 7598-91-6 ]

[ 7598-91-6 ] Synthesis Path-Upstream 1~2

1
[ 7598-91-6 ]
[ 13314-85-7 ]

Reference： [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 14, p. 3094 - 3102
[2] Research on Chemical Intermediates, 2010, vol. 36, # 8, p. 975 - 983
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 3, p. 867 - 891
[4] Journal of the Chemical Society, 1951, p. 2029,2031
[5] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 15, p. 1991 - 1996

2
[ 7598-91-6 ]
[ 131707-24-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3744 - 3748

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Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: ethyl 5-hydroxy-2-methylindole-3-carboxylate With water; sodium hydroxide In tetrahydrofuran for 48h; Reflux; Stage #2: With hydrogenchloride In water
	With sodium hydroxide

Yield	Reaction Conditions	Operation in experiment
68%	With acetic acid at 10 - 15℃; for 6h;
55%	With acetic acid at 20 - 45℃; for 5h;	Ethyl 5-Hydroxy-2-methylindole-3-carboxylate (Indole 1) To a solution of 1,4-Benzoquinone (27 g, 0.25 mole) in 450 mL of glacial acetic acid was added ethyl 3-aminocrotonate (16.2 g, 0.125 mole) portion-wise by controlling the reaction temperature below 45 °C using ice-water bath. The reaction mixture was stirred at room temperature for 5 hours. The precipitated solid was washed with acetic acid and water to give 17 g (62%) of gray crystalline solid, further washing with acetic acid gave off white solid with 55% yield. ^NMR (600 MHz, DMSOd6) 11.51 (s, 1H), 8.82 (s, 1H), 7.31 (d, J = 2.4 Hz, 1H), 7.13 (d, / = 8.52 Hz, 1H), 6.60 (dd, J = 2.4, 8.6 Hz, 1H), 4.24 (q, / = 7.08 Hz, 2H), 2.59 (s, 3H), 1.33 (t, J = 7.08 Hz, 3H); 13C NMR (150 MHz, DMSOd6) £165.2, 152.2, 144.4, 128.9, 127.9, 111.4, 111.2, 105.2, 102.1, 58.4, 14.5, 13.8.
	With chloroform

	With benzene
	With acetone
	With 1,2-dichloro-ethane
	Nenitzescu reaction conditions;

Yield	Reaction Conditions	Operation in experiment
96%	With pyridine for 1h; Inert atmosphere; Reflux;	Ethyl^' 5-aceioxy-2-methyM tf-indo3earboxylate 1a: Acetic anhydride (25,9 ml, 274 mmc- 20 eq.) was added to a stirred solution of ethyl 5-hydroxy-2-methy\|-1 W-lndole-3-carbo ylate 1 (3.00 g, 13.6 mmoi, 1 ,0 eq.) in pyridine (3,32 mL, 41 .1 mmoi, 3.0 eq,) and the reaction heated to reflux. After 1 h, the reaction was allowed to cool back to rt before pouring- the mixture into a solution of aqueous saturated sodium bicarbonate (40 mL). The product .was. extracted with ethyl acetate (3 x 40 ml) and the combined organic layers, were washed with wate (40 mL), to yield the product as a white solid which was used without. further purification (3.4 g, 96%). NM : δ (40Q MHz, CDCls) 8.34 (1 H, s; H), 7.75 (1H, s, }, 7.21 (1 H , d, J 8.5, He), 6.89 (1 H, d, J 8.5, 7 4.38 (2H, q, J 7.1 , C02CH2CH3), 2.71 (3H, e, CiCH3), 2.34 (3H, s, CqaCH3), 1.43 (3H, t, J 7.1 , CO20H2C3). c (100 MHz, CQCb) 170.8 (CG2CH3}, 165.8 (COaEt), 1.45.9 (Gs), 145.3 (G2), 132.4 (C8). 127,9 {C3), 116.3 (C6), 113.8 (C<>, 111.2
75%	With pyridine at 50℃; for 3h;
74%	With pyridine for 1h; Reflux;

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