[ CAS No. 1256825-86-1 ] {[proInfo.proName]}

Name: 1256825-86-1|Methyl 1H-pyrrolo[2,3-b]pyridine-6-carboxylate|95%
Brand: Ambeed
SKU: A176114
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Quality Control of [ 1256825-86-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1256825-86-1 ]

SDS Specification

Alternatived Products of [ 1256825-86-1 ]

Product Details of [ 1256825-86-1 ]

CAS No. :	1256825-86-1	MDL No. :	MFCD00006743
Formula :	C₉H₈N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XNOPDFAJQROROS-UHFFFAOYSA-N
M.W :	176.17	Pubchem ID :	57475482
Synonyms :

Calculated chemistry of [ 1256825-86-1 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.11
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	47.37
TPSA :	54.98 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) :	-6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.63
Log Po/w (XLOGP3) :	1.5
Log Po/w (WLOGP) :	1.35
Log Po/w (MLOGP) :	0.9
Log Po/w (SILICOS-IT) :	1.84
Consensus Log Po/w :	1.44

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.26
Solubility :	0.974 mg/ml ; 0.00553 mol/l
Class :	Soluble
Log S (Ali) :	-2.26
Solubility :	0.963 mg/ml ; 0.00547 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.98
Solubility :	0.183 mg/ml ; 0.00104 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.65

Safety of [ 1256825-86-1 ]

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 [ 1256825-86-1 ]

* 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 [ 1256825-86-1 ]
Downstream synthetic route of [ 1256825-86-1 ]

[ 1256825-86-1 ] Synthesis Path-Upstream 1~2

1
[ 898746-35-5 ]
[ 18107-18-1 ]
[ 1256825-86-1 ]

Reference： [1] Patent: WO2012/93101, 2012, A1, . Location in patent: Page/Page column 132

2
[ 189882-33-5 ]
[ 1256825-86-1 ]

Reference： [1] Patent: CN104387385, 2016, B,

[ 1256825-86-1 ] Synthesis Path-Downstream 1~20

1
[ 67-56-1 ]
[ 898746-35-5 ]
[ 1256825-86-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; for 18.0h;Reflux;	To a solution of 1 H-pyrrolo[2,3-b]pyridine-6-carboxylic acid (1g; Allweys) in MeOH (30 ml) was added concentrated sulfuric acid (0.2 ml) and the reaction mixture was heated under reflux for 18 hr. The reaction mixture was cooled and partitioned between EtOAc (100 ml) and aqueous sodium bicarbonate (50 ml). The organic layer was dried over magnesium sulphate, filtered and evaporated to afford the title compound (470mg) as a pale brown solid, m/z [M+H]+: 177.0. Retention time 0.70 min (LC/MS method 3).
127 g	With sulfuric acid; at 70℃;	176 g of 7-azaindole-6-carboxylic acid was added with stirring under mechanical stirring to a mixture of methanol 1.9Liter, then 80 ml of concentrated sulfuric acid was slowly added, heated, refluxed at 70 C overnight, HPLCDetection, to the raw material reaction completely, stop the reaction, naturally reduced to room temperature.Post-processing:The reaction solution was poured into 5 liters of ice water and suction filtered. The filter cake was washed with 500 ml of water and added to 2 liters of water,Adjusted to pH 7-8 with saturated sodium bicarbonate solution, stirred for 30 minutes, filtered and the filter cake washed with 500 ml of water,Dried under reduced pressure to obtain 127 g of methyl 7-azaindole-6-carboxylate (2). Samples were taken and HPLC showed pure

Reference： [1]Patent: WO2011/12622,2011,A1 .Location in patent: Page/Page column 109
[2]Patent: CN104387385,2016,B .Location in patent: Paragraph 0040; 0046-0049
[3]Journal of Medicinal Chemistry,2019,vol. 62,p. 831 - 856

2
[ 1256825-86-1 ]
[ 1263413-97-3 ]

Yield	Reaction Conditions	Operation in experiment
		To a suspension of <strong>[1256825-86-1]methyl 1H-pyrrolo[2,3-b]pyridine-6-carboxylate</strong> (200 mg; may be prepared as described in intermediate 169) in MeOH (10 ml) was added lithium borohydride (74 mg) and the reaction mixture was stirred at room temperature for 30 min. Lithium borohydride (74 mg) was added and the mixture was heated at 5O0C for 15 hr. Lithium borohydride (148 mg) and the mixture was heated at 5O0C for 24 hr. Lithium borohydride (small amounts portionwise over six hours, approximately 300 mg) was added and the mixture was heated at 5O0C for 72 hr. Lithium borohydride (small amounts portionwise over six hours, approximately 300 mg) was added and the mixture was heated at 5O0C for 24 hr. The reaction mixture was cooled and left at RT for 2 days. The solvent was evaporated and the residue dissolved in aqueous hydrochloric acid (2 N, 20 ml). The aqueous was washed with EtOAc (2 x 30 ml). The aqueous was basified with 12.5 N aqueous sodium hydroxide to pH 14 and then extracted with DCM (3 x 25 ml). The organic layer was dried over magnesium sulfate, filtered and evaporated to give an off-white solid (42mg). This was purified by MDAP to afford the title compound (32 mg) as a white solid. 1H NMR (CD3OD) delta: 4.74 (2H, s), 6.45 (1 H, d), 7.22 (1 H, d), 7.33 (1 H, d), 7.97 (1 H, d). Retention time 0.57 min (LC/MS method 4).

Reference： [1]Patent: WO2011/12622,2011,A1 .Location in patent: Page/Page column 109; 110

3
[ 898746-35-5 ]
[ 18107-18-1 ]
[ 1256825-86-1 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; diethyl ether; at 0 - 20℃; for 0.5h;	To a stirred solution of 1 H-pyrrolo[2,3-b]pyridine-6-carboxylic acid [898746-35-5] (500 mg, 3.08 mmol) in MeOH was added a 2M solution of trimethylsilyldiazomethane in Et20 at 0C, and the reaction mixture was stirred at RT for 30 min. The reaction mixture was concentrated in vacuo to give the title compound. MS (LC/MS): 177 [M+H]+, 375 [2M+H]+; tR (HPLC conditions k): 2.71

Reference： [1]Patent: WO2012/93101,2012,A1 .Location in patent: Page/Page column 132

Yield	Reaction Conditions	Operation in experiment
82%	In tetrahydrofuran; diethyl ether; at 20℃; for 0.5h;	General procedure: The compound (750mg, 3.8mmol) obtained from Preparation Example 7-1 was dissolved in tetrahydrofuran (150ml), and 0.25M solution of diazomethane in diethyl ether (18.4ml, 4.6mmol) was slowly added thereto. The mixture was stirred at room temperature for 30 minutes and distilled under reduced pressure to obtain the title compound (800mg, 99%).

5
[ 1256825-86-1 ]
methyl 3,3-dibromo-2-oxo-7-azaindole-6-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85 g	With pyridinium hydrobromide perbromide; In tert-butyl alcohol; at 40℃; for 2.0h;	Bromine oxidation reaction:With 5 liters three bottles,Under mechanical agitation,60 g of 7-azaindole-6-carboxylic acid methyl ester,After adding 3.7 liters of tert-butanol,When the temperature was raised to 40 C,545 g of pyridine hydrobromide perbromide(PBPB) were added portionwise,At the end of 1 hour.And then kept at 40 C for 1 hour.Sampling monitoring,HPLC showed a starting material / product ratio of no more than 1%. Post-treatment and recrystallization:The reaction solution was poured into 5 liters of ice water, extracted with ethyl acetate (5 liters) at a temperature of 5 C, and the organic layer was collected.The mixture was concentrated to a volume of 1/3 solvent and poured into 3 liters of ice water. The solid was precipitated, filtered and the cake was washed with 500 ml of water and dried. Recrystallization was carried out using a 1: 5 weight ratio of ethyl acetate to methanol,Filtration,After drying under reduced pressure,Methyl 3,3-dibromo-2-oxo-7-azaindole-6-carboxylate (3), 85 g was obtained and sampled and HPLC showed a purity of 90%

Reference： [1]Patent: CN104387385,2016,B .Location in patent: Paragraph 0040; 0050-0054

6
[ 189882-33-5 ]
[ 1256825-86-1 ]

Reference： [1]Patent: CN104387385,2016,B

7
[ 1256825-86-1 ]
methyl 3-iodo-1H-pyrrolo[2,3-b]pyridine-6-carboxylate [ No CAS ]