[ CAS No. 800401-70-1 ] {[proInfo.proName]}

Name: 800401-70-1|Ethyl 5-bromo-1H-pyrrolo-[2,3-c]-pyridine-2-carboxylate|97%
Brand: Ambeed
SKU: A381665
Rating: 90 (40 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 800401-70-1 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 800401-70-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 800401-70-1 ]

SDS Specification

Alternatived Products of [ 800401-70-1 ]

Product Details of [ 800401-70-1 ]

CAS No. :	800401-70-1	MDL No. :	MFCD12031217
Formula :	C₁₀H₉BrN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	INZFCWYCQKQUMU-UHFFFAOYSA-N
M.W :	269.10	Pubchem ID :	50998338
Synonyms :

Calculated chemistry of [ 800401-70-1 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.2
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	59.88
TPSA :	54.98 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.24
Log Po/w (XLOGP3) :	2.56
Log Po/w (WLOGP) :	2.5
Log Po/w (MLOGP) :	1.23
Log Po/w (SILICOS-IT) :	2.85
Consensus Log Po/w :	2.28

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.37
Solubility :	0.116 mg/ml ; 0.000429 mol/l
Class :	Soluble
Log S (Ali) :	-3.36
Solubility :	0.117 mg/ml ; 0.000434 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.25
Solubility :	0.0153 mg/ml ; 0.0000569 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.2

Safety of [ 800401-70-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H317-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 800401-70-1 ]

* 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 [ 800401-70-1 ]
Downstream synthetic route of [ 800401-70-1 ]

[ 800401-70-1 ] Synthesis Path-Upstream 1~4

1
[ 800401-69-8 ]
[ 800401-70-1 ]

Reference： [1] Patent: WO2004/104001, 2004, A2, . Location in patent: Page 40

2
[ 95-92-1 ]
[ 23056-47-5 ]
[ 800401-70-1 ]

Reference： [1] Patent: WO2004/104001, 2004, A2, . Location in patent: Page 40-41

3
[ 21901-41-7 ]
[ 800401-70-1 ]

Reference： [1] Patent: WO2004/104001, 2004, A2,
[2] Patent: WO2004/104001, 2004, A2,

4
[ 23056-47-5 ]
[ 800401-70-1 ]

Reference： [1] Patent: WO2004/104001, 2004, A2,

[ 800401-70-1 ] Synthesis Path-Downstream 1~40

1
[ 95-92-1 ]
[ 23056-47-5 ]
[ 800401-70-1 ]

Yield	Reaction Conditions	Operation in experiment
		Route B : To a solution of 2-bromo-4-methyl-5-nitropyridine (Preparation 24, 5.7g, 26.3mmol) in diethyl oxalate (17.9mL) under argon was added 1,8- diazabicyclo [5,4, 0] undec-7-ene (4. 5ML, 30.2mmol) to give a dark red precipitate. Reaction mixture was stirred at rt for 4. 5h and concentrated in vacuo. Acetic acid (140ML) was added to the residue under argon and heated to 60C. Iron (2.94g, 52.6mmol) was added in small portions over a period of LH. he reaction mixture was heated at 80C for 4h. The reaction mixture was cooled to rt and poured into water (300mL) which gave a beige precipitate. The precipitate was isolated and washed with water. The solid obtained was dissolved in ethyl acetate (700ML) and filtered. The filtrate was concentrated in vacuo to give the title compound. m/z (ES+) = 269 [M+ H] + ; RT = 3. 39MIN.

Reference： [1]Patent: WO2004/104001,2004,A2 .Location in patent: Page 40-41

2
[ 557-21-1 ]
[ 800401-70-1 ]
5-cyano-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	tetrakis(triphenylphosphine) palladium(0); In DMF (N,N-dimethyl-formamide); for 4.5h;Heating / reflux;	To a solution OF 5-BROMO-LH-PYRROLO [2,3-c] pyridine-2-carboxylic acid ethyl ester (Preparation 26,0. 160g, 0. 590MMOL) in DMF (anhydrous, 5ML) was added zinc (II) cyanide (0.041g, 0.35mmol) then tetrakis-triphenylphosphine palladium (0). The reaction mixture was degassed by bubbling argon through it for l Omin. The reaction mixture was heated to reflux temperature for 4. 5h then allowed to cool to rt. Water (30mL) was added and the mixture extracted with ethyl acetate (2X50ML). The combined organics were washed with brine (30mL), dried (MGS04), filtered and concentrated in vacuo. The residue was dissolved in ethyl acetate then adsorbed onto silica gel. Purification via flash column chromatography (SI02, ethyl acetate: isohexane, 1: 3, v/v) gave the title compound as a white solid. aH (CDCl3): 1.45 (3H, t), 4.49 (2H, quartet), 7.31 (1H, s), 8.09 (1H, s), 8.97 (1H, s), 9.60 (1H, br s); M/Z (ES+) = 216 [M+ H] + ; RT = 3. 03MIN.

Reference： [1]Patent: WO2004/104001,2004,A2 .Location in patent: Page 53

3
[ 800401-70-1 ]
[ 1066-54-2 ]
[ 800401-85-8 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In 1,4-dioxane; at 20℃; for 24h;	PdCl2 (PPh3) 2 (0.026g, 0.037mmol) and Cu (I) I (0.007g, 0. 037MMOL) were added sequentially to 5-BROMO-LH-PYRROLO [2,3-c] pyridine-2-carboxylic acid ethyl ester (Preparation 26, 0. 100G, 0.370mmol) under an argon atmosphere. 1,4-Dioxane (7mL, anhydrous) followed by DIISOPROPYLAMINE (0.063mL, 0. 45MMOL) were added and the stirred mixture was purged with argon for 5min. Trimethylsilylacetylene (0.064mL, 0. 45MMOL) was added dropwise and the resulting mixture stirred at rt for 24h. The reaction mixture was partitioned between water (50ML) and ethyl acetate (LOOML) and the layers separated. The aqueous phase was extracted with ethyl acetate (3X30ML). The combined organics were washed with brine (50ML), dried (MGS04), filtered and concentrated in vacuo. The residue was dissolved in the minimum amount of dichloromethane and loaded onto a silica column. Purification via flash column chromatography (SI02, dichloromethane then 25% ethyl acetate/ isohexane) gave a pale yellow solid. 8H (CDCl3): 0.28 (9H, s), 1.43 (3H, t), 4.45 (2H, q), 7. 18 (1H, s), 7.83 (1H, s), 8.86 (1H, s), 9.21 (1H, br s).

Reference： [1]Patent: WO2004/104001,2004,A2 .Location in patent: Page 51-52

4
[ 800401-69-8 ]
[ 800401-70-1 ]

Yield	Reaction Conditions	Operation in experiment
	With iron; ammonium chloride; In tetrahydrofuran; ethanol; water; for 2h;Heating / reflux;	Route A: To a solution OF 3- (2-BROMO-5-NITROPYRIDIN-4-YL)-2-OXOPROPIONIC acid ethyl ester (Preparation 25,3. 38g, 10.7mmol) in THF (50ML) and ethanol (LOOML) was added saturated ammonium chloride solution (50ML) and iron powder (3.57g, 64. 0mmol) and the reaction heated under reflux for 2h. The reaction mixture was filtered through celite and washed several times with ethyl acetate. The solvent was removed in vacuo and the remainder partitioned between saturated sodium hydrogen carbonate solution (lOOmL) and ethyl acetate (3 x 150mL). The combined organic fractions were dried (MgS04) and concentrated in vacuo to give the title compound as ABROWN SOLID. AH (CD30D): 1.42 (3H, t), 4.43 (2H, q), 7.14 (1H, s), 7.85 (1H, s), 8.58 (1H, s); m/z (ES+) = 269 [M+ H] +.

Reference： [1]Patent: WO2004/104001,2004,A2 .Location in patent: Page 40

5
[ 800401-70-1 ]
5-bromo-1 H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; water; In ethanol; for 1.5h;Heating / reflux;	Sodium hydroxide solution (L. lmL, 2M, 2.23mmol) was added to a solution of 5-BROMO-LH-PYRROLO [2,3-c] pyridine-2-carboxylic acid ethyl ester (Preparation 26, 500MG, 1. 86MMOL) in ethanol (20mL), and the reaction mixture heated under reflux for 1. 5h and then concentrated in vacuo. The residue was dissolved in water (15ML) and acidified with acetic acid resulting in formation of a brown precipitate. The solid was collected by filtration and dried to give the title compound as a brown SOLID. AH (d6 DMSO): 7.08 (1H, s), 7.97 (1H, s), 8.60 (1H, s); m/z (ES+) = 241 [M+ H] +.

Reference： [1]Patent: WO2004/104001,2004,A2 .Location in patent: Page 41

6
[ 800401-70-1 ]
ethyl 5-ethynyl-1-methyl-1H-pyrrolo[2,3-c]pyridine-2-carboxylate [ No CAS ]