1065181-58-9|Ethyl 5-bromo-1H-indole-7-carboxylate| Ambeed

CAS No. :	1065181-58-9
Formula :	C₁₁H₁₀BrNO₂
M.W :	268.11
SMILES Code :	O=C(C1=CC(Br)=CC2=C1NC=C2)OCC
MDL No. :	MFCD21608002
InChI Key :	YVPFHVKOHMYAHB-UHFFFAOYSA-N
Pubchem ID :	59332585

Safety of [ 1065181-58-9 ]

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

Computational Chemistry of [ 1065181-58-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	9
Fraction Csp3	0.18
Num. rotatable bonds	3
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	62.09
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	42.09 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.68
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	2.96
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.11
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.	2.36
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	3.37
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.9

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.61
Solubility	0.0654 mg/ml ; 0.000244 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.51
Solubility	0.0835 mg/ml ; 0.000311 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	-4.62
Solubility	0.00646 mg/ml ; 0.0000241 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	Yes
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	No
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.	-5.83 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	0.0
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	0.0 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)	1.8

Application In Synthesis of [ 1065181-58-9 ]

* 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 [ 1065181-58-9 ]

[ 1065181-58-9 ] Synthesis Path-Downstream 1~55

1
[ 496-15-1 ]
[ 1065181-58-9 ]

References: [1]Patent: WO2008/118724,2008,A1 .

2
tetrahydrothiophene-3-carbaldehyde [ No CAS ]
[ 1065181-58-9 ]
[ 1065183-53-0 ]

Yield	Reaction Conditions	Operation in experiment
56.4%		Intermediate 104:Ethyl 5-bromo-3-(tetrahydro-3-thienylmethyl)-1 H-indole-7-carboxylate.To a solution of tetrahydro-3-thiophenecarbaldehyde (5.0 g, 43.10 mmol) in dichloromethane (200 mL) was added TMS-OTf (15.4 mL, 86.26 mmol) and ethyl 5- bromo-1 H-indole-7-carboxylate (11.5 g, 43.10 mmol) dropwise at 0 0C. The mixture was stirred at 0 0C for 2h, and then triethylsilane was added at the same temperature, which was maintained for 2h. The reaction was warmed to 20 0C and stirred for 16h. Water was added, the layers were separated, and the organic layer was (Na2SO4),concentrated, and purified on silica gel (PE:EA = 50:1 ), giving 9g (56.4) of the title compound. 1H NMR (CDCI3): delta 1.43 (t, 3H), 2.08 (m, 1 H), 2.58 (m, 2H), 2.88 (m, 6H), 4.44 (q, 2H), 7.09 (s, 1 H), 7.89 (s, 1 H), 7.95 (s, 1 H), 9.65 (s, 1 H).

References: [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 123.

3
[ 2323-13-9 ]
[ 1065181-58-9 ]
[ 1065182-83-3 ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate 72:(racem/cJ-Ethyl 5-bromo-3-(2,2-dimethyltetrahydro-2H-thiopyran-4-yl)-1H-indole-7- carboxylate.2,2-Dimethyltetrahydro-4H-thiopyran-4-one (0.675 g, 4.68 mmol) was placed in a dried flask fitted up with an addition funnel, a septum and an argon inlet, and dissolved in dry DCM (15 mL), cooled to 0 0C, stirred, and then trimethylsilyl trifluoromethanesulfonate (1.692 mL, 9.36 mmol) was added dropwise through the addition funnel over 10 minutes. DCM (5 mL) was used to wash the addition funnel walls. To this mixture was added dropwise ethyl 5-bromo-1 H-indole-7- carboxylate (1.341 g, 5 mmol) in DCM (15 mL) over 2 hours. Then triethylsilane (2.98 mL, 18.73 mmol) was added in one portion. The mixture was stirred 2 h at 0 0C, and left stirring at 23 0C overnight. The reaction was <n="108"/>quenched with a saturated aqueous solution of sodium bicarbonate, and the resulting biphasic mixture extracted with DCM to give 2.1 15 g of the title compound. LC/MS: m/z 398.0 (M+H), Rt 1.49 min.

References: [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 105-106.

4
[ 19090-03-0 ]
[ 1065181-58-9 ]
[ 1065182-38-8 ]

Yield	Reaction Conditions	Operation in experiment
40%		Intermediate 53:Ethyl 5-bromo-3-(tetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxylate.Dihydro-2H-thiopyran-3(4/-/)-one (0.217g, 1.86mmol) was dissolved in dichloromethane (23ml_) in an oven dried flask containing 3 A molecular sieves and stirred under argon at 00C. TMS-OTf (0.414g, 1.86mmol, 0.33 ml.) was added slowly to the mixture over 10 min.Ethyl 5-bromo-1 /-/-indole-7-carboxylate (0.5g, 1.86mmol) was dissolved in DCM (7ml_) and added to the reaction via syringe pump over 2 hours, after which it was stirred for 3 hours between 0 and 10 0C. The reaction was cooled to 0 0C and triethylsilane (0.325g, 0.44ml_, 2.8mmol) was added all at once and the reaction was stirred at room temperature for 18 hours. The reaction was then quenched with a saturated sodium bicarbonate solution and extracted with DCM. The combined organics were washed with water. The combined aqueous layers were back-extracted with DCM. The combined organics were washed with brine, dried with MgSO4, and concentrated. The crude compound was purified on a Combiflash silica column with 5-25% EA/Hexane to give 0.279g (40%) of the title compound.LC/MS: m/z 369 (M+H), Rt 2.74 min.

References: [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 96.
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.

5
[ 143262-10-6 ]
[ 1065181-58-9 ]

References: [1]Patent: WO2008/118724,2008,A1 .
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.

6
[ 1072-72-6 ]
[ 1065181-58-9 ]
[ 1065181-66-9 ]

Yield	Reaction Conditions	Operation in experiment
76%		The title compound can also be prepared according to the following procedure: TMSOTf (1.4 ml_, 7.7 mmol) was added dropwise to a solution of tetrahydro-4H-thiopyran- 4-one (0.88 g, 7.6 mmol) in DCM (80 ml.) in the presence of molecular sieves at 0 0C (bath temp). A solution of ethyl 5-bromo-1 /-/-indole-7-carboxylate (2 g, 7.4 mmol). in DCM (20 ml.) was added and the reaction was stirred for 15 min. Triethylsilane (2 ml_, 12.5 mmol) was added and the reaction was allowed to warm to room temperature overnight. Saturated aqueous Na2CO3 was added, the layers separated and the aqueous layer extracted with DCM. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The residue was washed with MeOH and dried in a vacuum oven, giving 2.07 g (76%) of the title compound.

References: [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 71.
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.

7
[ 1003-04-9 ]
[ 1065181-58-9 ]
[ 1065181-97-6 ]

Yield	Reaction Conditions	Operation in experiment
47%		Intermediate 25:Ethyl 5-bromo-3-(tetrahydro-3-thienyl)-1H-indole-7-carboxylate.Dihydro-3(2H)-thiophenone (0.381 g, 3.73mmol) was dissolved in dichloromethane (50ml) in an oven dried flask containing 3A molecular sieves and stirred under Argon at O0C. TMS-OTf (0.826g, 3.73mmol, 0.67 ml.) was added slowly to the mixture over 10 min. Ethyl 5-bromo-1 /-/-indole-7-carboxylate (1 g, 3.73mmol) was dissolved in DCM (6 ml.) and added to the reaction via syringe pump over 2 hours, after which it was stirred for 30 min at 0 0C. Triethylsilane (0.651 g, 0.89ml, 5.59mmol) was then added all at once and the reaction was stirred at room temperature for 18 hours. The reaction was then quenched with a saturated sodium bicarbonate solution (35 ml.) and extracted with DCM (2 x 50 ml_). The combined organics were washed with water (2 x 100 ml_), brine, dried with MgSO4, and concentrated. The crude compound was purified on Combiflash silica column with 10% EA/Hexane to give 0.62Og (47%) of the title compound. LCMS m/z =355 (M+H), RT = 1.34 min.

References: [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 81.

8
[ 2323-17-3 ]
[ 1065181-58-9 ]
[ 1065182-49-1 ]

Yield	Reaction Conditions	Operation in experiment
26%		Intermediate 59:Ethyl S-bromo-S^jtheta-dimethyltetrahydro^H-thiopyran^-ylJ-IH-indole-y-carboxylate.2,6-Dimethyltetrahydro-4H-thiopyran-4-one (0.293g, 2.03mmol) was dissolved in dichloromethane (35ml_) in an oven dried flask containing 3 A molecular sieves and stirred under argon at 0 0C. TMS-OTf (0.451 g, 2.03mmol, 0.36 ml.) was added slowly to the mixture over 10 min. Ethyl 5-bromo-1 /-/-indole-7-carboxylate (0.293g, 2.031 mmol) was dissolved in DCM (1OmL) and added to the reaction via syringe pump over 2 hours, after which it was stirred for 3 hours between 0 and 10 0C. The reaction was cooled to 0 0C and triethylsilane (0.353 g, 0.485 ml_, 3.04 mmol) was then added all at once and the reaction was stirred at room temperature overnight. The reaction was then quenched with a saturated sodium bicarbonate solution, filtered, then extracted with DCM. The combined organics were washed with water. The combined aqueous layers were back-extracted with DCM. The combined organics were washed with brine, dried with MgSO4, and concentrated. The crude compound was purified on Combiflash silica column with 0-30% EA/DCM to give 0.212g (26%) of the the title compound. LC/MS: m/z 397 (M+H), Rt 1.51 min.

References: [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 99.

9
[ 22072-22-6 ]
[ 1065181-58-9 ]
[ 1065182-26-4 ]

Yield	Reaction Conditions	Operation in experiment
24%		Intermediate 46: Ethyl 5-bromo-3-(4-thiepanyl)-1H-indole-7-carboxylate.To a solution of 4-thiepanone (900 mg, 6.9 mmol, 1.1 eq) in dry dichloromethane (30 ml.) was added activated molecular sieves (4 A, beads, spatula tip full) and the solution was cooled to O 0C using an ice water bath. Trimethylsilyl trifluromethanesulfonate (1.25 ml_, 6.9 mmol, 1.1 eq) was added dropwise to the ketone solution, followed by the dropwise addition of ethyl 5-bromo-1 /-/-indole-7-carboxylate (1.69g, 6.3 mmol, 1 eq) as a solution in dichloromethane (10 ml_). The reaction mixture was stirred at rt for 2h, then warmed to 35 0C for 45 minutes. The deep red reaction mixture was cooled to 0 0C and triethylsilane (2 ml_, 12.6 mmol, 2 eq) was added. The mixture was warmed to rt for 30 minutes, then was quenched by the addition of saturated aq. sodium bicarbonate. The aqueous layer was extracted with dichloromethane (2x50 ml_), and the combined organic extracts were dried over sodium sulfate, filtered through a thin pad of silica gel (to remove baseline impurities), eluting with 50% ethyl acetate in hexanes, and concentrated to afford the crude product as a yellow residue. The crude material was purified by lsco Combiflash, eluting with 0-30% ethyl acetate in hexanes (120 gram column). The title compound was obtained as a yellow residue (540 mg, 24%).

References: [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 92.

10
[ 1065181-56-7 ]
[ 1065181-58-9 ]

Yield	Reaction Conditions	Operation in experiment
69%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In chloroform; for 2h;Inert atmosphere;	Intermediate 4: Ethyl delta-bromo-IH-indole^-carboxylate. <n="69"/>DDQ (1 19.3 g. 525.7mmol) was added in several portions to a solution of ethyl 5-bromo- 2,3-dihydro-1 /-/-indole-7-carboxylate (129.1 g, 0.48 mmol) in CHCI3 (1500 ml.) and the mixture was stirred for 2 h. The reaction was filtered and the solid was washed with CHCI3 (3 x 500 ml_). The filtrate was washed with 5% NaOH (3 x 500 ml_), H2O (500 ml.) and brine (500 ml.) then dried over Na2SO4. The solution was evaporated and the residue was recrystallized with EtOH, giving 88 g (69%) of the title compound. LC/MS: m/z 267.6 (M+H), Rt 1.14 min.

References: [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 66-67.
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.

11
[ 1065181-58-9 ]
[ 1065182-40-2 ]

References: [1]Patent: WO2008/118724,2008,A1 .
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.

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[ 1065181-58-9 ]
[ 1065182-43-5 ]

References: [1]Patent: WO2008/118724,2008,A1 .
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.

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[ 1065181-58-9 ]
[ 1065182-45-7 ]

References: [1]Patent: WO2008/118724,2008,A1 .
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.

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[ 1065181-58-9 ]
[ 1065182-51-5 ]

References: [1]Patent: WO2008/118724,2008,A1 .

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[ 1065181-58-9 ]
[ 1065182-53-7 ]

References: [1]Patent: WO2008/118724,2008,A1 .

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[ 1065181-58-9 ]
[ 1065182-56-0 ]

References: [1]Patent: WO2008/118724,2008,A1 .

17
[ 1065181-58-9 ]
[ 1065182-70-8 ]

References: [1]Patent: WO2008/118724,2008,A1 .
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.

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[ 1065181-58-9 ]
[ 1065182-92-4 ]

References: [1]Patent: WO2008/118724,2008,A1 .
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.

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[ 1065181-58-9 ]
[ 1065182-79-7 ]
[ 1065182-75-3 ]

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[ 1065181-58-9 ]
[ 1065182-85-5 ]

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[ 1065181-58-9 ]
[ 1065182-87-7 ]

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22
[ 1065181-58-9 ]
[ 1065183-09-6 ]

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23
[ 1065181-58-9 ]
[ 1065183-11-0 ]

References: [1]Patent: WO2008/118724,2008,A1 .

24
[ 1065181-58-9 ]
[ 1065183-14-3 ]

References: [1]Patent: WO2008/118724,2008,A1 .

25
[ 1065181-58-9 ]
5-bromo-3-[cis-2-(1-methylethyl)-1,1-dioxidotetrahydro-2H-thiopyran-4-yl]-1H-indole-7-carboxamide [ No CAS ]
5-bromo-3-[trans-2-(1-methylethyl)-1,1-dioxidotetrahydro-2H-thiopyran-4-yl]-1H-indole-7-carboxamide [ No CAS ]

References: [1]Patent: WO2008/118724,2008,A1 .

26
[ 1065181-58-9 ]
[ 1065183-43-8 ]

References: [1]Patent: WO2008/118724,2008,A1 .

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[ 1065181-58-9 ]
[ 1065183-45-0 ]

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[ 1065181-58-9 ]
[ 1065183-54-1 ]

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[ 1065181-58-9 ]
[ 1065183-56-3 ]

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[ 1065181-58-9 ]
[ 1065183-59-6 ]

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[ 1065181-58-9 ]
[ 1065175-72-5 ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.

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[ 1065181-58-9 ]
[ 1065181-68-1 ]

References: [1]Patent: WO2008/118724,2008,A1 .
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.

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[ 1065181-58-9 ]
[ 1065181-70-5 ]

References: [1]Patent: WO2008/118724,2008,A1 .
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.

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[ 1065181-58-9 ]
[ 1065181-79-4 ]

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[ 1065181-58-9 ]
[ 1065181-82-9 ]

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[ 1065181-58-9 ]
[ 1065181-91-0 ]

References: [1]Patent: WO2008/118724,2008,A1 .
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.

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[ 1065181-58-9 ]
[ 1065181-94-3 ]

References: [1]Patent: WO2008/118724,2008,A1 .
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.

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[ 1065181-58-9 ]
[ 1065181-98-7 ]

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39
[ 1065181-58-9 ]
[ 1065179-21-6 ]

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40
[ 1065181-58-9 ]
[ 1065182-29-7 ]

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41
[ 1065181-58-9 ]
[ 1065182-32-2 ]

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42
[ 1065181-58-9 ]
[ 1065182-33-3 ]

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43
[ 1065181-58-9 ]
[ 1065185-56-9 ]

References: [1]Patent: WO2008/118724,2008,A1 .

44
[ 1065181-58-9 ]
[ 71747-22-3 ]
[ 1065183-06-3 ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate 80:Ethyl 5-Bromo-3-[2-(1 -methylethyl)tetrahydro-2H-thiopyran-4-yl]-1 H-indole-7- carboxylate.2-(1-methylethyl)tetrahydro-2H-thiopyran-4-one (1.185 g, 7.49 mmol) was dissolved in dry dichloromethane (DCM) (20 ml_), cooled in an ice bath to ca 0 0C, and stirred under argon. Trimethylsilyl trifluoromethanesulfonate (2.71 ml_, 14.98 mmol) was added dropwise over 10 minutes, and dry DCM (5 ml.) was used to wash in the last of the trimethylsilyltrifuoromethanesulfonate. To this mixture was added dropwise, a solution of ethyl 5-bromo-1 H-indole-7-carboxylate (2.145 g, 8 mmol) in dry DCM (20 ml_), and then an additional portion of dry DCM (5 ml.) was used to wash the last of ethyl 5-bromo-1 H- indole-7-carboxylate into the reaction. Triethylsilane (4.77 ml_, 30.0 mmol) was added to the reaction in one portion. The resulting mixture was stirred 2h at 0 0C, and left stirring at 23 0C overnight. The reaction was diluted with saturated aqueous sodium bicarbonate, and the resulting biphasic mixture was extracted with DCM, dried (MgSO4) and the DCM was removed in vacuo to give the title compound as a dark yellow oil. LC/MS: m/z 414.3 (M+H), Rt 1.58 min.

References: [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 110.

45
[ 1065181-58-9 ]
[ 76625-84-8 ]
ethyl 5-bromo-3-(2-phenyltetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxylate [ No CAS ]
ethyl 5-bromo-3-(2-phenyltetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate 87:Ethyl 5-bromo-3-(2-phenyltetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxylate.To a solution of 2-phenylthian-4-one (SJTU) (0.900 g, 4.68 mmol) in dichloromethane (DCM) (15 ml_), cooled on an ice bath to 0 0C, under argon, was added dropwise trimethylsilyl trifluoromethanesulfonate (1.807 ml_, 10 mmol) over 10 minutes, an additional portion of dry DCM (5 ml.) was used to wash the addition funnel walls. To this mixture ethyl 5-bromo-1 H-indole-7- carboxylate (1.340 g, 5.00 mmol) was added dropwise, in solution with of dry DCM, over 2 hours. Finally, triethylsilane (3.19 ml_, 20 mmol) was added in one portion and the mixture was stirred 2 h at ca 0 0C, and left stirring at 23 0C 16 h. The reaction was quenched with a saturated aqueous solution of sodium bicarbonate, and the resulting biphasic mixture partitioned with DCM to afford 2.21 g of brow gummy oil. LCMS of product may indicate an overlapping mixture of ca 5:2 major to minor isomers (cis/trans). LC/MS: m/z 448.1 (M+H), Rt 3.23 min.

References: [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 114.

46
[ 16892-50-5 ]
[ 1065181-58-9 ]
ethyl 5-bromo-3-(8-thiabicyclo[3.2.1]oct-3-yl)-1H-indole-7-carboxylate [ No CAS ]
ethyl 5-bromo-3-(8-thiabicyclo[3.2.1]oct-3-yl)-1H-indole-7-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate 31 :Ethyl 5-bromo-3-(8-thiabicyclo[3.2.1]oct-3-yl)-1H-indole-7-carboxylate.To a solution of 8-thiabicyclo[3.2.1]octan-3-one (1.33 g, 9.32 mmol, 1 eq) in dry dichloromethane (50 mL) was added a spatula tip full of activated 4A molecular sieves (beads). The ketone solution was cooled to 0 0C, and trimethylsilyl triflate (1.7 mL, 9.41 mmol, 1 eq) was added dropwise followed by a solution of ethyl 5-bromo-1 H-indole-7- carboxylate (2.5 g, 9.32 mmol, 1 eq) in dichloromethane (25 mL). The mixture was stirred at 23 0C overnight, then was cooled to 23 0C and triethylsilane (2.3 mL, 14.4 mmol, 1.5 eq) was added in a single portion. The reaction was stirred at 23 0C for 1.5h, then quenched by the addition of saturated aqueous sodium bicarbonate. The mixture was extracted with dichloromethane, and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The crude product was purified by lsco Combiflash, 120 gram column, eluting with 0-30% ethyl acetate in hexanes. The ethyl 5-bromo-3-(8- thiabicyclo[3.2.1]oct-3-yl)-1 /-/-indole-7-carboxylate was obtained as a mixture of isomers (2.38 g, 65%).

References: [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 84.

47
[ 61571-06-0 ]
[ 1065181-58-9 ]
[ 1065183-42-7 ]

Yield	Reaction Conditions	Operation in experiment
66%		Intermediate 98:Ethyl 5-bromo-3-(tetrahydro-2H-thiopyran-3-ylmethyl)-1H-indole-7-carboxylate.To a 100 ml. three-necked flask equipped with an addition funnel was added tetrahydro- 2H-thiopyran-3-carbaldehyde (2.50 g, 0.019 mol) and dry DCM (30 ml_). Trimethylsilyl trifluoromethanesulfonate was put in the addition funnel. The mixture was cooled down to0 0C with an ice bath and put under nitrogen atmosphere. Trimethylsilyl trifluoromethanesulfonate was added over 15 min, and 10 ml. of dry DCM were used to wash the addition funnel walls. A solution of ethyl 5-bromo-1 H-indole-7-carboxylate in 30 ml. dry DCM was added to the mixture for 2 h at 0 0C, and the mixture was then stirred at room tmperature overnight. An aqueous solution of sodium bicarbonate was added, the layers were separated, and the mixture was extracted with DCM (3 x 100 ml_). The combined organic layers were dried (Na2SO4), filtered, and purified by chromatography, eluting with a mixture of PE:EA (50:1-30:1 ) to afford 4.82 g (66.0%) of the title compound. 1H NMR NMR (CDCI3) delta 1.1 1-1.15 (m,1 H),1.43 (t,3H),1.65-1.71 (m,2H),1.83-1.87 (m,1 H),1.96-2.03 (m,2H), 2.32-2.38 (m,1 H), 2.51-2.59 (m, 2H),2.66-2.68 (m, 2H), 4.40-4.45 (q,2H), 7.07 (d, 1 H),7.77 (d, 1 H), 7.95 (d, 1 H), 9.64 (s, 1 H).

References: [1]Patent: WO2008/118724,2008,A1 .Location in patent: Page/Page column 120.

48
[ 1065181-52-3 ]
[ 1065181-58-9 ]

References: [1]Patent: WO2008/118724,2008,A1 .
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.

49
[ 63853-74-7 ]
[ 1065181-58-9 ]
ethyl 5-bromo-3-(5-oxopyrrolidin-2-yl)-1H-indole-7-carboxylate [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.

50
[ 1065181-58-9 ]
[ 70687-35-3 ]
ethyl 5-bromo-3-(1-methyl-5-oxopyrrolidin-2-yl)-1H-indole-7-carboxylate [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.

51
[ 67-56-1 ]
[ 3437-29-4 ]
[ 1065181-58-9 ]
[ 98-80-6 ]
3-(3,3-dimethyl-5-oxopyrrolidin-2-yl)-5-phenyl-1H-indole-7-carboxamide [ No CAS ]
3-(4,4-dimethyl-5-oxopyrrolidin-2-yl)-5-phenyl-1H-indole-7-carboxamide [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.

52
[ 67-56-1 ]
[ 3437-29-4 ]
[ 1065181-58-9 ]
ethyl 5-bromo-3-(4,4-dimethyl-5-oxopyrrolidin-2-yl)-1H-indole-7-carboxylate [ No CAS ]
ethyl 5-bromo-3-(3,3-dimethyl-5-oxopyrrolidin-2-yl)-1H-indole-7-carboxylate [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.

53
[ 67-56-1 ]
[ 3437-29-4 ]
[ 1065181-58-9 ]
5-bromo-3-(4,4-dimethyl-5-oxopyrrolidin-2-yl)-1H-indole-7-carboxylic acid [ No CAS ]
5-bromo-3-(3,3-dimethyl-5-oxopyrrolidin-2-yl)-1H-indole-7-carboxylic acid [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.

54
[ 67-56-1 ]
[ 3437-29-4 ]
[ 1065181-58-9 ]
5-bromo-3-(4,4-dimethyl-5-oxopyrrolidin-2-yl)-1H-indole-7-carboxamide [ No CAS ]
5-bromo-3-(3,3-dimethyl-5-oxopyrrolidin-2-yl)-1H-indole-7-carboxamide [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.

55
[ 1065181-58-9 ]
[ 16892-50-5 ]
ethyl 5-bromo-3-(8-thiabicyclo[3.2.1]oct-3-yl)-1H-indole-7-carboxylate [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1164 - 1169.

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

Related Functional Groups of
[ 1065181-58-9 ]

Bromides

A139356 [860624-89-1]

Methyl 5-bromoindole-7-carboxylate

Similarity: 0.97

A122383 [1224724-39-3]

Methyl 4-bromo-1H-indole-7-carboxylate

Similarity: 0.92

A268689 [860624-90-4]

5-Bromo-1H-indole-7-carboxylic acid

Similarity: 0.91

A119898 [860624-88-0]

Methyl 5-bromoindoline-7-carboxylate

Similarity: 0.88

A122404 [885523-35-3]

Methyl 7-bromo-1H-indole-5-carboxylate

Similarity: 0.87

Esters

A139356 [860624-89-1]

Methyl 5-bromoindole-7-carboxylate

Similarity: 0.97

A122383 [1224724-39-3]

Methyl 4-bromo-1H-indole-7-carboxylate

Similarity: 0.92

A119898 [860624-88-0]

Methyl 5-bromoindoline-7-carboxylate

Similarity: 0.88

A101336 [882679-96-1]

Methyl 4-bromo-1H-indole-6-carboxylate

Similarity: 0.87

A122404 [885523-35-3]

Methyl 7-bromo-1H-indole-5-carboxylate

Similarity: 0.87

Related Parent Nucleus of
[ 1065181-58-9 ]

Indoles

A139356 [860624-89-1]

Methyl 5-bromoindole-7-carboxylate

Similarity: 0.97

A122383 [1224724-39-3]

Methyl 4-bromo-1H-indole-7-carboxylate

Similarity: 0.92

A268689 [860624-90-4]

5-Bromo-1H-indole-7-carboxylic acid

Similarity: 0.91

A101336 [882679-96-1]

Methyl 4-bromo-1H-indole-6-carboxylate

Similarity: 0.87

A122404 [885523-35-3]

Methyl 7-bromo-1H-indole-5-carboxylate

Similarity: 0.87

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P321
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P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
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P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
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P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
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P370	In case of fire:
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P378
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
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P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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P401
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P413
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Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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Environmental hazards
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 1065181-58-9

{[proInfo.proName]}

CAS No.: 1065181-58-9

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CAS No.: 1065181-58-9

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[ 1065181-58-9 ] Synthesis Path-Downstream 1~55

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