[ CAS No. 877-03-2 ] {[proInfo.proName]}

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2D 3D

Structure of 877-03-2 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 877-03-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 877-03-2 ]

SDS Specification

Alternatived Products of [ 877-03-2 ]

Product Details of [ 877-03-2 ]

CAS No. :	877-03-2	MDL No. :	MFCD00152016
Formula :	C₉H₆BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PEENKJZANBYXNB-UHFFFAOYSA-N
M.W :	224.05	Pubchem ID :	70137
Synonyms :

Calculated chemistry of [ 877-03-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	51.39
TPSA :	32.86 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) :	-6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.59
Log Po/w (XLOGP3) :	2.2
Log Po/w (WLOGP) :	2.74
Log Po/w (MLOGP) :	1.6
Log Po/w (SILICOS-IT) :	3.33
Consensus Log Po/w :	2.29

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.1
Solubility :	0.176 mg/ml ; 0.000787 mol/l
Class :	Soluble
Log S (Ali) :	-2.52
Solubility :	0.67 mg/ml ; 0.00299 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.09
Solubility :	0.0182 mg/ml ; 0.0000811 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.22

Safety of [ 877-03-2 ]

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

Application In Synthesis of [ 877-03-2 ]

* 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.

Downstream synthetic route of [ 877-03-2 ]

[ 877-03-2 ] Synthesis Path-Downstream 1~7

1
[ 877-03-2 ]
[ 74-88-4 ]
[ 10102-94-0 ]

Yield	Reaction Conditions	Operation in experiment
96%		5-bromoindole-3-carbaldehyde 2 (10 mmol) was dissolved in acetonitrile and to this powdered NaOH (5 mmol) was added and stirred for 10 min. Methyl iodide (10 mmol) was added dropwise to the reaction mixture. After 3h of stirring at room temperature, the solvent was completely evaporated. It was extracted with ethyl acetate (3x20 ml) and dried over Na2SO4. The combined organic layer was concentrated in vacuo to give a light yellow color solid purified by recrystallization with diethyl ether. Pale yellow solid; Yield: 96%; mp 122-124 C; IR (KBr) numax 3103, 2923, 2813, 1700, 1654. 1533, 1467, 1369, 1083, 799, 726; 1H NMR (DMSO-d6, 300 MHz) delta 9.88 (s, 1H), 8.33 (s, 1H), 8.23 (d, J = 1.70 Hz, 1H), 7.60 (d, J = 8.68 Hz, 1H), 7.48 (dd, J = 2.08, 8.87 Hz, 1H), 3.89 (s, 3H); TOF-HRMS (m/z) for C10H8BrNO, calculated 237.9862, observed 237.9855 [M+1] +
91%	With sodium hydride; In tetrahydrofuran; at 0℃; for 1.83333h;	5-Bromo-1-methyl-lH-indole-3-carbaldehyde; 5-Bromo-1H-indole-3-carbaldehyde (4.8 mmol, 1076 mg) was dissolved in 15 mL of THF and the solution was cooled to 0 C under N2-athmosphere. Sodium hydride (11.7 mmol, 280 mg) was added carefully in portions and iodomethane (8.1 mmol, 1150 mg) was added. The mixture was stirred at 0 C for 1 h. More iodomethane (8.1 mmol, 1150 mg) was added and the stirring continued for 50 min. The mixture was poured over ice and the resulting slurry was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and evaporated. This gave 1037 mg (91 %) of the title product. 'H NMR (400 MHz, MeOH-d4) 8 9.82 (s, 1H), 8,29 (m, 1H), 8.06 (s, 1H), 7.43 (m, 2H), 3.89 (s, 3H)
81%		General procedure: To a suspension of NaH 60% in oil (2.25 equiv.) in dry DMF(0.8 mL/mmol) was added, at 0 C and under nitrogen atmosphere, a solution of indolecarboxaldehyde (1 equiv.) in dry DMF (2.5 mL/mmol). After stirring for 30 min at rt, alkyl halide (1.0e3.0 equiv.)was slowly added. After stirring overnight, the reaction wasquenched by addition of water and the product was extracted withdiethyl ether. The organic layer was dried over MgSO4, filtered offand concentrated under vacuum. The crude product was purifiedby column chromatography on silica gel.

		General procedure: Compounds 7-9 were synthesized from the corresponding compounds 4-6. A solution of compounds 4-6 (60 mmol) in THF (30 mL) were added dropwise to a suspension of NaH (3.60 g, 60% dispersion in mineral oil, 150 mmol) in THF (30 mL) at 0 C. After stirring for 15 min, the heterogeneous mixture was treated with iodomethane (5.04 mL, 79.2 mmol) at room temperature for 1 h. Then the reaction mixture was cooled to 0 C, quenched with saturated NH4Cl (60 mL), and extracted with ether (3 * 50 mL). The organic layers were combined, washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to give 1-Methyl-1H-indole-3-carboxaldehyde (7-9), a light brown solid. The crude 7-9 were used in the next step without any further purification.
	With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 24h;	General procedure: The relevant indole-3-carboxaldehyde (2a-c, 10 mmol) in THF(25 mL) was added dropwise to a stirred solution of NaH (25 mmol)in THF (25 mL) at 0 C and CH3I (13.2 mmol) was added after 15 minstirring. The reaction mixturewas moved to room temperature andstirred for further 24 h. Then the solvent was removed in vacuumand the residue was extracted by ethyl acetate. The organic layerwas washed with brine, dried over anhydrous sodium sulfate,filtered and concentrated in vacuum. Recrystallization affordedcompound 3a-c with yields of 93.4-97.5%.

Reference： [1]Tetrahedron,2005,vol. 61,p. 1793 - 1801
[2]Journal of Medicinal Chemistry,2009,vol. 52,p. 6217 - 6223
[3]European Journal of Medicinal Chemistry,2001,vol. 36,p. 545 - 553
[4]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 3024 - 3028
[5]Patent: WO2005/66132,2005,A1 .Location in patent: Page/Page column 47
[6]European Journal of Medicinal Chemistry,2016,vol. 122,p. 408 - 418
[7]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1793 - 1798
[8]European Journal of Medicinal Chemistry,2015,vol. 99,p. 125 - 137
[9]ChemMedChem,2016,vol. 11,p. 1446 - 1458
[10]European Journal of Medicinal Chemistry,2018,vol. 156,p. 722 - 737
[11]Organic Letters,2019,vol. 21,p. 2048 - 2051

2
[ 877-03-2 ]
[ 105-58-8 ]
[ 10102-94-0 ]

Reference： [1]Chemical Biology and Drug Design,2011,vol. 77,p. 182 - 188

3
[ 877-03-2 ]
[ 77-78-1 ]
[ 10102-94-0 ]

Reference： [1]Heteroatom Chemistry,2012,vol. 23,p. 41 - 48
[2]Synthetic Communications,2012,vol. 42,p. 1746 - 1759
[3]Journal of Chemical Sciences,2011,vol. 123,p. 609 - 614
[4]Journal of Heterocyclic Chemistry,2019,vol. 56,p. 92 - 98

4
[ 877-03-2 ]
[ 75-18-3 ]
[ 10102-94-0 ]

Reference： [1]Asian Journal of Chemistry,2013,vol. 25,p. 8741 - 8748

5
[ 877-03-2 ]
DMS [ No CAS ]
[ 10102-94-0 ]

Reference： [1]Medicinal Chemistry Research,2014,vol. 23,p. 1569 - 1580

6
[ 5654-97-7 ]
[ 877-03-2 ]
C₁₆H₁₀BrN₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate; In ethanol; at 20℃;	General procedure: Various aldehydes (1.0 equiv) were added to stirred solutions of indolin-2-one, 5-chloroindolin-2-one or <strong>[5654-97-7]7-azaoxindole</strong> (1.0equiv) in absolute ethanol. After stirring at room temperature for 5 min NaOEt/EtOH (0.5 mL) was added and the mixture was then stirred at room temperature overnight. The solvent was then removed under vacuum. The residue was washed with saturated sodium chloride solution and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under vacuum. The solid part was purified by chromatography over silica gel using ethyl acetate/petroleum ether as the eluent to afford desired compounds 1a-1g, 2a, 3a.

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 6953 - 6960

7
[ 877-03-2 ]
[ 10406-06-1 ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium permanganate; water; In acetone; at 20℃; for 6.5h;	General procedure: 6 g of substituted indole-3-aldehydes (10a-b) was dissolved in 600 mL of acetone.To this KMnO4 (9 g, 56 mmol) soluble in 180 mL water was added slowly for 30 min and the reaction mixture was allowed for stirring for 6 h at room temperature. After it was quenched by 6 mL of 30% H2O2, filtered and concentrated on rotavapor. Now it was solidified by conc.HCl, filtered, dried and recrystallized from methanol solvent which then afforded 5-substituted indole-3-carboxylic acids 11a-b. 5-Bromo-1H-indole-3-carboxylic acid (11b) (Yoo et al.2012) yellow color solid. yield: 65%. m.p: 230-232 C; IR (KBr): 3349, 2914, 2574, 1643 cm-1; 1H NMR (400 MHz, DMSO-d6): delta 7.30 (1H, m, Ar-H), 7.435 (1H, d, J = 8.8 Hz, Ar-H), 8.05 (1H, d, J = 2.8 Hz, Ar-H), 8.12 (1H, d, J = 2 Hz, Ar-H), 12.01 (1H, bs, -NH), 12.13 (1H, s, -OH) ppm; 13C NMR (400 MHz, DMSO-d6): delta 107.06, 113.79, 114.28, 122.68, 124.70, 127.79, 133.45, 135.16, 165.45 ppm; HRMS calculated for C9H6NO2BrNa: 261.94741; found: 261.94711.
65%	With potassium permanganate; In acetone; at 20℃; for 6.5h;	General procedure: 6 g of substituted indole e 3e aldehydes (6a-6b) were respectively dissolved in 600 mL ofacetone. KMnO4 solution (9 g KMnO4 soluble in 180 mL water) wasadded dropwise for 30 min to this reaction mixture and the reactionmass was stirred for 6 h at room temperature. The reactionmixture was then quenched by adding 20 mL of 30% H2O2, filteredand concentrated on rotavapor. Later, it was acidified by conc. HCl,filtered, dried and recrystallized from methanol. 5 e substitutedindole e 3 e carboxylic acids 7a-7b was obtained as the product.

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 2745 - 2763
[2]Chemical Papers,2018,vol. 72,p. 1369 - 1378
[3]Journal of Molecular Structure,2020,vol. 1208
[4]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 1043 - 1055

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Isomers

Technical Information

• Alkyl Halide Occurrence • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Julia-Kocienski Olefination • Kinetics of Alkyl Halides • Knoevenagel Condensation • Kumada Cross-Coupling Reaction • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Historical Records

Related Functional Groups of
[ 877-03-2 ]

Bromides

[ 98600-34-1 ]

4-Bromoindole-3-carboxyaldehyde

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[ 10406-06-1 ]

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Aldehydes

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4-Bromoindole-3-carboxyaldehyde

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6-Bromo-1H-indole-3-carbaldehyde

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Related Parent Nucleus of
[ 877-03-2 ]

Indoles

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4-Bromoindole-3-carboxyaldehyde

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6-Bromo-1H-indole-3-carbaldehyde

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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 877-03-2 ] {[proInfo.proName]}

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Druglikeness

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[ 877-03-2 ] Synthesis Path-Downstream 1~7

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Bromides

Aldehydes

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[ 877-03-2 ]