[ CAS No. 69047-36-5 ]

Name: 69047-36-5|1-Methyl-1H-indole-7-carbaldehyde|97%
Brand: Ambeed
SKU: A365830
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3d Animation Molecule Structure of 69047-36-5

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Quality Control of [ 69047-36-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 69047-36-5 ]

SDS Specification

Alternatived Products of [ 69047-36-5 ]

Product Details of [ 69047-36-5 ]

CAS No. :	69047-36-5	MDL No. :	MFCD11109329
Formula :	C₁₀H₉NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JOBIAZYEJOMXEP-UHFFFAOYSA-N
M.W :	159.19	Pubchem ID :	11040979
Synonyms :

Calculated chemistry of [ 69047-36-5 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.1
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	48.59
TPSA :	22.0 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) :	-6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.74
Log Po/w (XLOGP3) :	1.46
Log Po/w (WLOGP) :	1.99
Log Po/w (MLOGP) :	1.18
Log Po/w (SILICOS-IT) :	2.09
Consensus Log Po/w :	1.69

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.24
Solubility :	0.925 mg/ml ; 0.00581 mol/l
Class :	Soluble
Log S (Ali) :	-1.53
Solubility :	4.72 mg/ml ; 0.0296 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.78
Solubility :	0.264 mg/ml ; 0.00166 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.05

Safety of [ 69047-36-5 ]

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

Application In Synthesis of [ 69047-36-5 ]

* 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 [ 69047-36-5 ]
Downstream synthetic route of [ 69047-36-5 ]

[ 69047-36-5 ] Synthesis Path-Upstream 1~8

1
[ 1074-88-0 ]
[ 74-88-4 ]
[ 69047-36-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide for 0.333333 h; Inert atmosphere Stage #2: at 20℃; for 12 h;	EXAMPLE I 1-methyl-1H-indole-7-carbaldehyde 20 g 1H-indole-7-carbaldehyde are dissolved in 160 ml N,N-dimethylformamide and combined batchwise with 15.5 g potassium-tert.-butoxide under argon. After the addition has ended the mixture is left for 20 minutes with stirring and then 8.7 ml methyl iodide are added dropwise. Then the mixture is left for 12 hours at ambient temperature with stirring and then distributed between water and ethyl acetate. The aqueous phase is twice extracted with ethyl acetate and the combined organic phases are washed with saturated aqueous sodium chloride solution. After drying with magnesium sulphate the solvents are eliminated in vacuo. The residue is extracted from water. The solid thus obtained is suction filtered and dried in vacuo. Yield: 20 g (91percent of theory) Mass spectrum (ESI⁺): m/z=160 [M+H]⁺
84%	Stage #1: With caesium carbonate In acetonitrile at 60℃; for 2 h; Stage #2: at 60℃; for 1 h;	General procedure: To a solution of indole-aldehyde (435mg 3mmol) in CH₃CN (30mL) was added Cs₂CO₃ (829mg, 6mmol), and the mixture was refluxed for 2h. To this solution, alkyl halide (3.3mmol) was added, and the mixture was heated under reflux for 1h. After the completion of the reaction, the solvent was evaporated under reduced pressure and water was added to the reaction mixture and extracted 3 times for ethyl acetate. The combined organic layers were dried over Na₂SO₄ and concentrated under vacuum. The residue was purified by flash chromatography.

Reference： [1] Patent: US2011/269737, 2011, A1, . Location in patent: Page/Page column 40
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 7, p. 2060 - 2079
[3] Patent: WO2004/52890, 2004, A1, . Location in patent: Page 92-93
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4533 - 4539
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 12, p. 5115 - 5129

2
[ 1074-88-0 ]
[ 77-78-1 ]
[ 69047-36-5 ]

Reference： [1] Tetrahedron Letters, 2003, vol. 44, # 14, p. 2903 - 2905
[2] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 14, p. 2261 - 2267
[3] Patent: WO2009/143058, 2009, A1, . Location in patent: Page/Page column 64

3
[ 69047-35-4 ]
[ 69047-36-5 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995, vol. 34, # 4, p. 285 - 288

4
[ 577-19-5 ]
[ 69047-36-5 ]

Reference： [1] Journal of Organometallic Chemistry, 2011, vol. 696, # 5, p. 1072 - 1083

5
[ 53951-34-1 ]
[ 69047-36-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4533 - 4539

6
[ 552-89-6 ]
[ 69047-36-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4533 - 4539

7
[ 51417-51-7 ]
[ 69047-36-5 ]

Reference： [1] Journal of Organometallic Chemistry, 2011, vol. 696, # 5, p. 1072 - 1083

8
[ 68-12-2 ]
[ 280752-68-3 ]
[ 69047-36-5 ]

Reference： [1] Journal of Organometallic Chemistry, 2011, vol. 696, # 5, p. 1072 - 1083

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H200	Unstable explosive
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Yield	Reaction Conditions	Operation in experiment
91%		EXAMPLE I 1-methyl-1H-indole-7-carbaldehyde 20 g 1H-indole-7-carbaldehyde are dissolved in 160 ml N,N-dimethylformamide and combined batchwise with 15.5 g potassium-tert.-butoxide under argon. After the addition has ended the mixture is left for 20 minutes with stirring and then 8.7 ml methyl iodide are added dropwise. Then the mixture is left for 12 hours at ambient temperature with stirring and then distributed between water and ethyl acetate. The aqueous phase is twice extracted with ethyl acetate and the combined organic phases are washed with saturated aqueous sodium chloride solution. After drying with magnesium sulphate the solvents are eliminated in vacuo. The residue is extracted from water. The solid thus obtained is suction filtered and dried in vacuo. Yield: 20 g (91% of theory) Mass spectrum (ESI+): m/z=160 [M+H]+
84%		General procedure: To a solution of indole-aldehyde (435mg 3mmol) in CH3CN (30mL) was added Cs2CO3 (829mg, 6mmol), and the mixture was refluxed for 2h. To this solution, alkyl halide (3.3mmol) was added, and the mixture was heated under reflux for 1h. After the completion of the reaction, the solvent was evaporated under reduced pressure and water was added to the reaction mixture and extracted 3 times for ethyl acetate. The combined organic layers were dried over Na2SO4 and concentrated under vacuum. The residue was purified by flash chromatography.
		To a solution of indole-7-carboxaldehyde (500 mg, 3.45 mmol) in DMF (8 ML) was added sodium hydride (152 mg of 60% dispersion in oil, 3.8 mmol). The mixture was stirred for 30 mins. Methyl iodide (0.98 g, 6.9 mmol) was then added and the mixture was stirred for 2 hrs. Ethyl acetate (200 mL) was added and solution was washed with H20 (3 x 20 mL) and brine (25 mL) dried over MGS04 and concentrated to afford N-methylindole-7- carboxaldehyde as a brown oil which was used without further purification. The crude oil was dissolved in anhydrous methanol (10 mL). Methylamine (5.1 mL OF 2M solution in methanol, 9.55 mmol) was added and the mixture was stirred for 3 hours. The solution was concentrated to a yellow oil and then dissolved into anhydrous methanol (10 mL). Sodium borohydride (131 mg, 3.45 mmol) was added and the mixture was stirred overnight. Water (1 mL) was added and the solution was concentrated to an orange oil. Sodium hydroxide (5 mL, 1N) was added and the product was extracted with ethyl acetate (3 x 20 mL), dried over MGS04 and concentrated to afford the title compound as a brown oil (400 mg, 68%). IH NMR (200 MHz, CDC13) 8 7.52 (dd, J= 7.0, 2.0 Hz, 1H), 7.23-6. 94 (m, 3H), 6.44 (d, J= 3.1 Hz, 1H), 4.10 (s, 3H), 4.04 (s, 2H), 2.51 (s, 3H).

[ CAS No. 69047-36-5 ]

Quality Control of [ 69047-36-5 ]

Related Doc. of [ 69047-36-5 ]

Product Details of [ 69047-36-5 ]

Calculated chemistry of [ 69047-36-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 69047-36-5 ]

Application In Synthesis of [ 69047-36-5 ]

[ 69047-36-5 ] Synthesis Path-Upstream 1~8

[ 69047-36-5 ] Synthesis Path-Downstream 1~69

Related Functional Groups of [ 69047-36-5 ]

Aldehydes

Related Parent Nucleus of [ 69047-36-5 ]

Indoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 69047-36-5 ]

Related Parent Nucleus of
[ 69047-36-5 ]