[ CAS No. 165250-69-1 ] {[proInfo.proName]}

Name: 165250-69-1|4-Methyl-5-nitro-1H-indole|97%
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SKU: A194438
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Quality Control of [ 165250-69-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 165250-69-1 ]

SDS Specification

Alternatived Products of [ 165250-69-1 ]

Product Details of [ 165250-69-1 ]

CAS No. :	165250-69-1	MDL No. :	MFCD11035915
Formula :	C₉H₈N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XRJNLFAXLSBIDS-UHFFFAOYSA-N
M.W :	176.17	Pubchem ID :	15453462
Synonyms :

Calculated chemistry of [ 165250-69-1 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.11
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	52.09
TPSA :	61.61 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) :	-5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.36
Log Po/w (XLOGP3) :	2.24
Log Po/w (WLOGP) :	2.38
Log Po/w (MLOGP) :	1.51
Log Po/w (SILICOS-IT) :	0.77
Consensus Log Po/w :	1.65

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.79
Solubility :	0.286 mg/ml ; 0.00162 mol/l
Class :	Soluble
Log S (Ali) :	-3.17
Solubility :	0.119 mg/ml ; 0.000677 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.05
Solubility :	0.157 mg/ml ; 0.000893 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.78

Safety of [ 165250-69-1 ]

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 [ 165250-69-1 ]

* 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 [ 165250-69-1 ]
Downstream synthetic route of [ 165250-69-1 ]

[ 165250-69-1 ] Synthesis Path-Upstream 1~3

1
[ 165250-69-1 ]
[ 196205-06-8 ]

Reference： [1] Patent: US5677321, 1997, A,

2
[ 6146-52-7 ]
[ 165250-69-1 ]

Yield	Reaction Conditions	Operation in experiment
4.1 mmol, 80%	With methylmagnesium bromide; chloranil In tetrahydrofuran	4-Methyl-5-nitroindole To a solution of 5-nitroindole (from Aldrich, 0.82 g, 5.1 mmol) in 20 mL of dry THF was added 5.0 mL (15 mmol) of methylmagnesium bromide for 0.5 h period and the resulting reaction mixture was stirred for 1 h at 25° C. Reaction was the quenched by adding a THF solution of tetrachloro-1,4-benzoquinone (1.2 g, 4.9 mmol). Reaction mixture was concentrated in vacuo, yielding a dark solid which was subjected to column chromatography (30percent EtOAc/n-Hexane) to yield 0.72 g (4.1 mmol, 80percent) of the desired product.

Reference： [1] Patent: US5677321, 1997, A,

3
[ 84-58-2 ]
[ 165250-69-1 ]

Reference： [1] Patent: US5521188, 1996, A,
[2] Patent: US5618816, 1997, A,

[ 165250-69-1 ] Synthesis Path-Downstream 1~14

1
4-methyl-5-nitroindoline [ No CAS ]
ethyl acetate n-hexane [ No CAS ]
[ 84-58-2 ]
[ 165250-69-1 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; dichloromethane;	D. 4-Methyl-5-nitroindole To a suspension of 4-methyl-5-nitroindoline (4.767 g, 0.0268 mol) in 100 mL of methanol was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (6.697 g, 0.0295 at room temperature for 1 h. The reaction mixture was then evaporated and the residue was taken up in dichloromethane. This solution was then washed with saturated aqueous NaHCO3 (*4), dried (Na2 SO4) and evaporated to give a solid. Crystallization of this material from ethyl acetate-hexane (-20 C.) afforded 4.161 g of the title compound as greenish-gold needles, mp 179-180 C. Chromatography of the mother liquor (SiO2 /ethyl acetate-hexane, 1:1) gave an additional 0.417 g of the pure product. Total yield=4.578 g (97%): IR (KBr) 3318, 1604, 1585 cm-; 1 H NMR (DMSO-d6, 200 MHz) delta 11.72 (br s, 1H), 7.81 (d, J=9.0 Hz, 1H), 7.56 (t, J=2.8 Hz, 1H), 7.39 (d, J=8.9 Hz, 1H), 6.79 (m, 1H), 2.75 (s, 3H). Anal. Calcd for C 9 H8 N2 O2: C, 61.35; H, 4.58; N, 15.90. Found: C, 61.32; H, 4.40; N, 15.96.
	In methanol; dichloromethane;	D. 4-Methyl-5-nitroindole To a suspension of 4-methyl-5-nitroindoline (4.767 g, 0.0268 mol) in 100 mL of methanol was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (6.697 g, 0.0295 mol) all at once and the resulting mixture was stirred at room temperature for 1 h. The reaction mixture was then evaporated and the residue was taken up in dichloromethane. This solution was then washed with saturated aqueous NaHCO3 (*4), dried (Na2 SO4) and evaporated to give a solid. Crystallization of this material from ethyl acetate-hexane (-20 C.) afforded 4.161 g of the title compound as greenish-gold needles, mp 179-180 C. Chromatography of the mother liquor (SiO2 /ethyl acetate-hexane, 1:1) gave an additional 0.417 g of the pure product. Total yield=4.578 g (97%): IR (KBr) 3318, 1604, 1585 cm-1; 1 H NMR (DMSO-d6, 200 MHz) delta11.72 (br s, 1H), 7.81 (d, J=9.0 Hz, 1H), 7.56 (t, J=2.8 Hz, 1H), 7.39 (d, J=8.9 Hz, 1H), 6.79 (m, 1H), 2.75 (s, 3H). Anal. Calcd for C9 H8 N2 O2: C, 61.35; H, 4.58; N, 15.90. Found: C, 61.32; H, 4.40; N, 15.96.

Reference： [1]Patent: US5521188,1996,A
[2]Patent: US5618816,1997,A

2
[ 2033-24-1 ]
[ 165250-69-1 ]
[ 147-85-3 ]
5-(4-Methyl-5-nitroindol-3-ylmethyl)-2,2-dimethyl-1,3-dioxane-4,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With formaldehyd; In acetonitrile;	5-(4-Methyl-5-nitroindol-3-ylmethyl)-2,2-dimethyl-1,3-dioxane-4,6-dione An adaption of the procedure of Flaugh was used. Thus, a solution of <strong>[165250-69-1]4-methyl-5-nitroindole</strong> (0.880 g, 5.00 mmol), Meldrum's acid (0.864 g, 6.00 mmol), 37% aqueous formaldehyde (0.5 mL, 6.0 mmol) and D,L-proline (0.029 g, 0.25 mmol) in 25 mL of acetonitrile was stirred at room temperature for 72 h. The resulting yellow slurry was stored at -20 C. and then the cold mixture was filtered. The filtercake was washed with cold acetonitrile and ether, and then it was dried in vacuo to give the title compound (1.055 g, 64%) as a canary-yellow solid, mp 196-198 C. (dec): IR (KBr) 3338, 1782, 1742 cm-1; 1 H NMR (DMSO-d6, 200 MHz) delta 11.46 (br s, 1H), 7.61 (d, J=8.9 Hz, 1H), 7.32 (d, J=8.9 Hz, 1H), 7.25 (d, J= 2.4 Hz, 1H), 4.74 (t, J=5.0 Hz, 1H), 3.64 (d, J=4.9 Hz, 1H), 2.80 (s, 3H), 1.84 (s, 3H), 1.69 (s, 3H). Anal. Calcd for C16 H16 N2 O6: C, 57.83; H, 4.85; N, 8.43. Found: C, 57.42; H, 4.68; N, 8.52.

Reference： [1]Patent: US5521188,1996,A

3
[ 165250-69-1 ]
[ 196205-06-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	palladium-carbon; In methanol;	4-Methyl-5-aminoindole A solution of <strong>[165250-69-1]4-methyl-5-nitroindole</strong> (0.72 g, 4.1 mmol) in 50 mL of methanol was stirred with 50 mg of 10% Pd/C under H2 for 12 h. Reaction mixture was filtered and concentrated in vacuo to provide an oil (0.61 g, >95%) which was characterized as the desired product by NMR analysis and subjected to a following reaction without further purification.

Reference： [1]Patent: US5677321,1997,A

4
[ 6146-52-7 ]
[ 165250-69-1 ]

Yield	Reaction Conditions	Operation in experiment
0.72 g (4.1 mmol, 80%)	With methylmagnesium bromide; chloranil; In tetrahydrofuran;	4-Methyl-5-nitroindole To a solution of 5-nitroindole (from Aldrich, 0.82 g, 5.1 mmol) in 20 mL of dry THF was added 5.0 mL (15 mmol) of methylmagnesium bromide for 0.5 h period and the resulting reaction mixture was stirred for 1 h at 25 C. Reaction was the quenched by adding a THF solution of tetrachloro-1,4-benzoquinone (1.2 g, 4.9 mmol). Reaction mixture was concentrated in vacuo, yielding a dark solid which was subjected to column chromatography (30% EtOAc/n-Hexane) to yield 0.72 g (4.1 mmol, 80%) of the desired product.

Reference： [1]Patent: US5677321,1997,A

Yield	Reaction Conditions	Operation in experiment
	With borane-THF; In tetrahydrofuran; at 20 - 50℃; for 1.75h;Cooling with ice; Inert atmosphere;	General procedure: [Reference Example 151] (0733) (0734) To the solution of 200 mg of 6-fluoro-5-nitro-1H-indole-2,3-dione in 4 mL of tetrahydrofuran, 2.2 mL of a 1.1 mol/L borane-tetrahydrofuran solution was added dropwise under ice-cooling and a nitrogen atmosphere, and the resultant was stirred at room temperature for one hour and 30 minutes and then stirred at 50C for 15 minutes. After cooling the reaction mixture to room temperature, water and 1 mL of 1 mol/L hydrochloric acid were added thereto dropwise, and the solvent was distilled off under reduced pressure. After adding ethyl acetate and water, the organic layer was separated, washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give 172 mg of 6-fluoro-5-nitro-1H-indole as a yellow brown solid. 1H-NMR (DMSO-d6) delta: 6.71 (1H, s), 7.47 (1H, d, J = 11.9 Hz), 7.60 (1H, s), 8.48 (1H, d, J = 7.3 Hz), 11.82 (1H, s). MS (ESI, m/z): 179 (M-H)-.

6
[ 165250-69-1 ]
tert-butyl 4-(1,4-dimethyl-5-nitro-1H-indol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]

Reference： [1]Patent: US2016/46597,2016,A1

7
[ 165250-69-1 ]
tert-butyl 4-(5-amino-1,4-dimethyl-1H-indol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]

Reference： [1]Patent: US2016/46597,2016,A1

8
[ 165250-69-1 ]
[ 74-88-4 ]
3-iodo-1,4-dimethyl-5-nitro-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%		To a cooled solution (ice-water bath) of <strong>[165250-69-1]4-methyl-5-nitroindole</strong> (1.76 g, 10 mmol) in DMF (30 mL) was added KOH pellets (0.78 g, 14 mmol). The cooling bath was removed, and the mixture was stirred at rt for 10 min. Iodine (2.79 g, 11 mmol) was added, and the stirring was continued for 5 h at room temperature. To this mixture was added potassium carbonate (3.17 g, 23 mmol) and methyl iodide (3.1 mL, 50 mmol), and stirring was continued at room temperature for 16 h. The mixture was diluted with water (150 mL), and treated with solid NaHSO3 with stirring until all excess iodine was quenched. The crude product was collected by filtration, washed with plenty of water, and dried.

Reference： [1]Patent: US2016/46597,2016,A1 .Location in patent: Paragraph 0286

9
[ 165250-69-1 ]
tert-butyl 4-(5-(3-cyanobenzamido)-1,4-dimethyl-1H-indol-3-yl)piperidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2016/46597,2016,A1

10
[ 165250-69-1 ]
C₉H₇IN₂O₂ [ No CAS ]