[ CAS No. 28737-29-3 ] {[proInfo.proName]}

Name: 28737-29-3|1-Ethyl-1H-indole-2-carboxylic acid|98%
Brand: Ambeed
SKU: A1111416
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3d Animation Molecule Structure of 28737-29-3

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Quality Control of [ 28737-29-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 28737-29-3 ]

SDS Specification

Alternatived Products of [ 28737-29-3 ]

Product Details of [ 28737-29-3 ]

CAS No. :	28737-29-3	MDL No. :	MFCD09037005
Formula :	C₁₁H₁₁NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FPVIIOSXSGECQO-UHFFFAOYSA-N
M.W :	189.21	Pubchem ID :	14384884
Synonyms :

Calculated chemistry of [ 28737-29-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.18
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	54.97
TPSA :	42.23 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) :	-5.82 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.81
Log Po/w (XLOGP3) :	2.3
Log Po/w (WLOGP) :	2.36
Log Po/w (MLOGP) :	1.67
Log Po/w (SILICOS-IT) :	1.64
Consensus Log Po/w :	1.96

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.85

Water Solubility

Log S (ESOL) :	-2.81
Solubility :	0.296 mg/ml ; 0.00156 mol/l
Class :	Soluble
Log S (Ali) :	-2.82
Solubility :	0.283 mg/ml ; 0.0015 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.63
Solubility :	0.448 mg/ml ; 0.00237 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.4

Safety of [ 28737-29-3 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 28737-29-3 ]

* 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 [ 28737-29-3 ]

[ 28737-29-3 ] Synthesis Path-Downstream 1~47

1
[ 67-56-1 ]
[ 28737-29-3 ]
[ 39243-32-8 ]

Reference： [1]Tetrahedron,1989,vol. 45,p. 3351 - 3362

2
[ 39243-30-6 ]
[ 28737-29-3 ]

Reference： [1]Tetrahedron,1989,vol. 45,p. 3351 - 3362

4
pyruvic acid ethylphenylhydrazone [ No CAS ]
[ 28737-29-3 ]

Reference： [1]Chemische Berichte,1897,vol. 30,p. 2816

5
[ 28737-29-3 ]
[ 917-54-4 ]
[ 172840-56-1 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 5298 - 5310

6
[ 40913-41-5 ]
[ 28737-29-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium hydroxide; In ethanol; at 20 - 50℃; for 3.0h;	130 mg (0.60 mol) of the compound prepared in the above step 1 was dissolved in ethanol, 2M sodium hydroxide was added, and the mixture was stirred at room temperature for 3 hours while heating to 50 C.After completion of the reaction, the reaction mixture was extracted with 50 ml of ethyl acetate, washed with 4N hydrochloric acid and water, and dried over anhydrous sodium sulfate.And concentrated under reduced pressure to obtain 106 mg (0.56 mmol) of the desired compound as a colorless solid in 93% yield.
90%		Compound 155b:; i-Ethyl-IH-indole-2-carboxylic acid 155bEster 155a (0.53g, 2.42 mmol) was refluxed in 10% NaOH (4.0 mL) and ethanol (8.0 mL) for one hour. The ethanol was removed in vacuo, and the water acidified to pH = 2 with 10% HCI. The resulting solids were filtered, washed with water, and dried to give 0.41 g (90%) of a white solid: 1H EPO <DP n="95"/>NMR (CDCI3): δ 7.71 (1 H, d, J = 8.1 Hz), 7.47 (1 H, s), 7.43-7.35 (2H, m), 7.18-7.14 (1 H, m), 4.64 (2H, q, J = 7.1 Hz), 1.42 (3H, t, J = 7.1 Hz). See Tetrahedron 45, 3351 (1989).

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 5298 - 5310
[2]Patent: KR101725451,2017,B1 .Location in patent: Paragraph 0306; 0313-0315
[3]Patent: WO2006/40646,2006,A1 .Location in patent: Page/Page column 93-94
[4]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5659 - 5663
[5]Journal of Organic Chemistry,2012,vol. 77,p. 6959 - 6969
[6]RSC Advances,2016,vol. 6,p. 21165 - 21186

7
[ 28737-29-3 ]
[ 672-58-2 ]
N-(1-ethyl-1H-indole-2-carbonyl)-3-trifluoromethyl-benzenesulfonamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5659 - 5663

8
[ 3770-50-1 ]
[ 28737-29-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 5659 - 5663
[2]Journal of Medicinal Chemistry,2004,vol. 47,p. 5298 - 5310
[3]RSC Advances,2016,vol. 6,p. 21165 - 21186
[4]Patent: KR101725451,2017,B1

9
[ 28737-29-3 ]
(Z)-methyl 4-(1-ethyl-1H-indol-2-yl)-2-hydroxy-4-oxobut-2-enoate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 5298 - 5310

10
[ 28737-29-3 ]
4-(1-ethyl-1H-indol-2-yl)-2-hydroxy-4-oxo-but-2-enoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 5298 - 5310

11
[ 548773-04-2 ]
[ 28737-29-3 ]
2-[[4-[4-[(4-bromophenyl)(ethoxyimino)methyl]-1-piperidinyl]-4-methyl-1-piperidinyl]carbonyl]-1-ethyl-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; HATU; In DMF (N,N-dimethyl-formamide); at 20℃; for 16.0h;	To a stirred solution OF 4- [ (4-BROMOPHENYL) (ethoxyimino) methyl]-1- (4-methyl-4- piperidinyl)-piperidine (50 mg, 0.12 MMOL), 1-ETHYL-1 H-INDOLE-2-CARBOXYLIC acid (25 mg, 0.13 MMOL), and Et3N (24.3 mg, 0.24 MMOL) in DMF (2 mL), HATU (61 mg, 0.16 MMOL) was added at room temperature. After 16 h the mixture was poured into ice water (10 mL), and was extracted with CH2CI2 (3X10 mL). The organic phase was dried over NA2SO4, and concentrated in vacuo. The crude product was purified by preparative TLC to afford the title compound.

Reference： [1]Patent: WO2004/113323,2004,A1 .Location in patent: Page 49

12
[ 884047-97-6 ]
[ 28737-29-3 ]
[ 884035-12-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With diisopropylamine; HATU; In N,N-dimethyl-formamide; at 0 - 20℃;	Example 155: Ethyl N-[(1-ethyl-1H-indol-2-yl)carbonyl]-3-(6-fluoro-1 H-indol-2-yl)-D-alaninate; 155The amine 103d (0.10g, 0.41 mmol) and acid 155b (0.078g, 0.41 mmol) were dissolved in DMF (1.5 mL ). Diisopropylamine (0.14 mL , 0.82 mmol) was added, and the reaction cooled to 0C. HATU (0.16g, 0.41 mmol) was added, and the reaction stirred at 0C two hours, then warmed to ambient temperature. The DMF was removed in vacuo, and the residue was dissolved in EtOAc/ sat. NaHCO3. The organic layer was separated, washed successively with water and brine, dried (MgSO4), and concentrated. The product was purified by flash silica gel chromatography (5-15% EtOAc/hexane) to afford 0.16g (90%) as a tan solid: mp = 128-130 C; Rf = 0.18 (30% EtOAc/hexane); 1H NMR (DMSO-d6): δ 11.15 (1 H, s), 8.89 (1H, d, J = 7.8 Hz), 7.63 (1H, d, J = 8.0 Hz), 7.52 (1 H, d, J = 8.3 Hz), 7.40-7.36 (1 H, m), 7.26-7.23 (1 H, m), 7.09-7.05 (3H, m), 6.78-6.73 (1 H, m), 6.26 (1 H, s), 4.83-4.77 (1 H, m), 4.46 (2H, q, J = 7.1 Hz), 4.14-4.08 (2H, m), 3.30-3.24 (2H, m), 1.16-1.10 (6H, m). MS 422 (M+H); Elemental Analysis for (C24H24N3O3F) calc: C 68.39, H 5.74, N 9.97; found: C 68.16, H 5.81 , N 9.84.

Reference： [1]Patent: WO2006/40646,2006,A1 .Location in patent: Page/Page column 95

13
[ 28737-29-3 ]
[ 2327-99-3 ]
[ 1393366-08-9 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 6959 - 6969

14
[ 28737-29-3 ]
[ 104-85-8 ]
C₂₈H₂₅N₃ [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 12008 - 12011

15
[ 109-74-0 ]
[ 28737-29-3 ]
C₂₄H₂₅N₃ [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 12008 - 12011

16
[ 28737-29-3 ]
N-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-1-ethyl-N-methyl-1H-indole-2-carboxamide [ No CAS ]

Reference： [1]Beilstein Journal of Organic Chemistry,2015,vol. 11,p. 1360 - 1366

17
[ 28737-29-3 ]
N-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-N,1-diethyl-1H-indole-2-carboxamide [ No CAS ]

Reference： [1]Beilstein Journal of Organic Chemistry,2015,vol. 11,p. 1360 - 1366

18
[ 28737-29-3 ]
N-(1,3-diethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-1-ethyl-N-methyl-1H-indole-2-carboxamide [ No CAS ]

Reference： [1]Beilstein Journal of Organic Chemistry,2015,vol. 11,p. 1360 - 1366

19
[ 28737-29-3 ]
C₁₁H₁₀ClNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride; N,N-dimethyl-formamide; In benzene; at 20℃; for 3.0h;	General procedure: To a stirred solution of 1 equiv. of indole-2-carboxylic acid 1 in 10 mL of dry benzene containing 2 drops of N, N-dimethylformamide, 1.5 equiv. of oxalyl chloride was added. The resulting solution was stirred at rt for 3 h, subsequently, the solvent was removed under reduced pressure and taken up in 5 mL of dry THF. In a separate flask, 1 equiv. of 5-amino uracil derivative 3 dissolved in 3 mL of dry THF was added to a suspension of 1.2 equiv. of NaH in 5 mL of dry THF at 0 C. The solution was allowed to stir at 0 oC for 30 min and the preformed acid chloride 2 was added drop wise. The resulting solution was allowed to warm to rt and stirred for 2 h. The solution was quenched with water and extracted with DCM. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The crude residue was subjected to flash silica gel chromatography to give the corresponding amide 4.

Reference： [1]Beilstein Journal of Organic Chemistry,2015,vol. 11,p. 1360 - 1366

20
[ 28737-29-3 ]
7-ethyl-1,3,5-trimethyl-5,7-dihydro-1H-pyrimido[4',5':5,6]pyrido[3,4-b]indole-2,4,6(3H)-trione [ No CAS ]

Reference： [1]Beilstein Journal of Organic Chemistry,2015,vol. 11,p. 1360 - 1366

21
[ 28737-29-3 ]
5,7-diethyl-1,3-dimethyl-5,7-dihydro-1H-pyrimido[4',5':5,6]pyrido[3,4-b]indole-2,4,6(3H)-trione [ No CAS ]

Reference： [1]Beilstein Journal of Organic Chemistry,2015,vol. 11,p. 1360 - 1366

22
[ 28737-29-3 ]
1,3,7-triethyl-5-methyl-5,7-dihydro-1H-pyrimido[4',5':5,6]pyrido[3,4-b]indole-2,4,6(3H)-trione [ No CAS ]

Reference： [1]Beilstein Journal of Organic Chemistry,2015,vol. 11,p. 1360 - 1366

23
[ 28737-29-3 ]
[ 14542-93-9 ]
[ 105-07-7 ]
[ 22483-09-6 ]
C₃₂H₄₂N₄O₄ [ No CAS ]