[ CAS No. 276862-85-2 ] {[proInfo.proName]}

Name: 276862-85-2|1H-Pyrrolo[3,2-b]pyridine-3-carbaldehyde|97%
Brand: Ambeed
SKU: A178433
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Quality Control of [ 276862-85-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 276862-85-2 ]

CAS No. :	276862-85-2	MDL No. :	MFCD11877845
Formula :	C₈H₆N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JDIWXZAFVHTGBQ-UHFFFAOYSA-N
M.W :	146.15	Pubchem ID :	17964132
Synonyms :

Calculated chemistry of [ 276862-85-2 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.48
TPSA :	45.75 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) :	-6.82 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.99
Log Po/w (XLOGP3) :	0.53
Log Po/w (WLOGP) :	1.38
Log Po/w (MLOGP) :	-0.05
Log Po/w (SILICOS-IT) :	2.17
Consensus Log Po/w :	1.0

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.62
Solubility :	3.51 mg/ml ; 0.024 mol/l
Class :	Very soluble
Log S (Ali) :	-1.06
Solubility :	12.7 mg/ml ; 0.0867 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.84
Solubility :	0.213 mg/ml ; 0.00146 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.24

Safety of [ 276862-85-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 276862-85-2 ]

* 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.

Upstream synthesis route of [ 276862-85-2 ]
Downstream synthetic route of [ 276862-85-2 ]

[ 276862-85-2 ] Synthesis Path-Upstream 1~1

1
[ 272-49-1 ]
[ 100-97-0 ]
[ 276862-85-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	for 4 h; Reflux	A mixture of 4-azaindole (0.500 g; 4.223 mmol), hexamethylenetetramine (0.890 g; 6.348 mmol) and acetic acid (3.630 mL; 63.45 mmol) in water (9 mL) was refluxed for 4 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. Purification by flash chromatography on silica gel using a gradient of methanol (2percent to 4percent) in dichloromethane furnished 0.550 g (89percent) of 1 /-/-pyrrolo[3,2-£>]pyridine-3-carbaldehyde. ESI/APCI(+): 147 (M+H). ESI/APCI(-): 145 (M-H).
56%	With acetic acid In water for 4 h; Heating / reflux	A mixture of 1H-pyrrolo[3,2-b]pyridine (947 mg, 8.02 mmol), hexamethylenetetramine (1.7 g, 12 mmol) and acetic acid (7.5 mL) in water (14 mL) was refluxed under N₂ for 4 hours. The reaction mixture was cooled to RT, concentrated, and the residue was purified via flash chromatography (DCM/MeOH/NH₄OH) affording 1H-Pyrrolo[3,2-b]pyridin-3-carbaldehyde as a white solid (660 mg, 56percent yield).

Reference： [1] Patent: WO2013/45516, 2013, A1, . Location in patent: Page/Page column 198
[2] Patent: US2007/123535, 2007, A1, . Location in patent: Page/Page column 35
[3] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 21, p. 5924 - 5934

[ 276862-85-2 ] Synthesis Path-Downstream 1~48

2
[ 272-49-1 ]
[ 100-97-0 ]
[ 276862-85-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	With water; acetic acid; for 4h;Reflux;	A mixture of 4-azaindole (0.500 g; 4.223 mmol), hexamethylenetetramine (0.890 g; 6.348 mmol) and acetic acid (3.630 mL; 63.45 mmol) in water (9 mL) was refluxed for 4 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. Purification by flash chromatography on silica gel using a gradient of methanol (2% to 4%) in dichloromethane furnished 0.550 g (89%) of 1 /-/-pyrrolo[3,2-£>]pyridine-3-carbaldehyde. ESI/APCI(+): 147 (M+H). ESI/APCI(-): 145 (M-H).
79%	With water; acetic acid; for 6h;Reflux;	To a stirred mixture of compound (1) (20 g, 169.2 mmol) and hexamethylenetetramine (HMTA) (72 g, 507.8 mmol) in 80 mL acetic acid, 160 mL of H2O and was heated to reflux for 6 hours. After completion of the reaction, the reaction mass was cooled to room temperature, a large number of solid precipitations were filtered and then the filter cake was washed with water and dried to give a white solid. The crude compound obtained was recrystallized from hexane to get the pure compound 3, 19.6 g with 79% in yield.
56%	With acetic acid; In water; for 4h;Heating / reflux;	A mixture of 1H-pyrrolo[3,2-b]pyridine (947 mg, 8.02 mmol), hexamethylenetetramine (1.7 g, 12 mmol) and acetic acid (7.5 mL) in water (14 mL) was refluxed under N2 for 4 hours. The reaction mixture was cooled to RT, concentrated, and the residue was purified via flash chromatography (DCM/MeOH/NH4OH) affording 1H-Pyrrolo[3,2-b]pyridin-3-carbaldehyde as a white solid (660 mg, 56% yield).

With water; acetic acid;Inert atmosphere; Reflux;

To a stirred solution containing 1.50 g (12.7 mmol) of 1H-pyrrolo[3,2-b]pyridine in 20 mL of 1:1 AcOH/H2O was added 2.67 g (19.0 mmol) of hexamethylenetetramine (HMTA). The reaction mixture was heated at reflux overnight under argon. The reaction mixture was cooled to 0 C and the formed precipitate was filtered and dried under vacuum. 1H-pyrrolo[3,2-b]pyridine-3-carbaldehyde (12) was obtained as a colorless solid and was used directly in the next step without further purification. To a stirred solution containing 487 mg (3.33 mmol) of 1H-pyrrolo[3,2-b]pyridine-3-carbaldehyde (12) in 20 mL of anhydrous DMF at 0 C was added 119 mg (4.99 mmol) of NaH. The reaction mixture was stirred at 0 C for 10 min under argon and then 954 mg (4.99 mmol) of p-TsCl was added. The reaction mixture was stirred at 0 C under argon for 3 h, diluted with 100 mL of NaHCO3 and extracted with two 50-mL portions of EtOAc. The combined organic phase was dried (MgSO4) and concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (10 × 4 cm). Elution with 4:1 hexanes/ethyl acetate gave 1-tosyl-1H-pyrrolo[3,2-b]pyridine-3-carbaldehyde (13) as an off-white solid: yield 691 mg (23% for two steps).

Reference： [1]Patent: WO2013/45516,2013,A1 .Location in patent: Page/Page column 198
[2]Synthetic Communications,2020,vol. 50,p. 71 - 84
[3]Patent: US2007/123535,2007,A1 .Location in patent: Page/Page column 35
[4]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5924 - 5934

3
[ 276862-85-2 ]
[ 120943-19-3 ]
[ 1234196-77-0 ]

Yield	Reaction Conditions	Operation in experiment
57%	With piperidine; acetic acid; In acetonitrile; at 20℃; for 24h;Heating / reflux;	A mixture of <strong>[276862-85-2]1H-pyrrolo[3,2-b]pyridin-3-carbaldehyde</strong> (660 mg, 4.5 mmol), tert-butyl-methyl malonate (3.8 mL, 22.5 mmol), piperidine (0.12 mL) and acetic acid (0.12 mL) in acetonitrile (40 mL) was heated to reflux. The resulting mixture was stirred at RT for 24 h, concentrated, and purified via flash chromatography (hexane/EtOAc) affording 2-(1H-Pyrrolo[3,2-b]pyridin-3-yl-methylene)-malonic acid tert-butyl ester methyl ester as a mixture of cis- and trans-isomers (780 mg, 57% yield).

Reference： [1]Patent: US2007/123535,2007,A1 .Location in patent: Page/Page column 35

4
[ 276862-85-2 ]
[ 74-88-4 ]
[ 860297-51-4 ]

Yield	Reaction Conditions	Operation in experiment
43%		b) 1-Methyl-lH-pyrrolo [3, 2-blpyridine-3-carbaldehyde; lH-Pyrrolo [3, 2-b] pyridine-3-carbaldehyde (63 mg, 0.43 mmol) was dissolved in 2 mL of DMF and sodium hydride (15 mg, 0.64 mmol) was added. After stirring for 5 min methyl iodide (61 mg, 0.43 mmol) was added and the reaction mixture was stirred for 1.5 h. The mixture was poured into water and extracted three times with EtOAc. The combined organic layer was washed with water, dried over Na2SO4 and evaporated. The crude product was chromatographed on a 1 g Isolute Si column with DCM/MeOH 95/5. Yield: 30 mg (43%). 'H NMR (300 MHz, CDC13) 8 10.24 (s, 1H), 8.60 (bd, 1H), 7.89 (s, 1H), 7.66 (d, 1H), 7.22 (m, 1H), 3.86 (s, 3H).

Reference： [1]Patent: WO2005/66132,2005,A1 .Location in patent: Page/Page column 88

5
[ 276862-85-2 ]
[ 1346151-39-0 ]
[ 1378263-33-2 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 5151 - 5164

6
[ 276862-85-2 ]
[ 1428969-55-4 ]

Reference： [1]Patent: WO2013/45516,2013,A1

7
[ 276862-85-2 ]
[ 24424-99-5 ]
[ 1428972-97-7 ]

Yield	Reaction Conditions	Operation in experiment
0.802 g	With dmap; In acetonitrile; at 20℃;	General procedure: To a solution of an appropriate indole, azaindole or alternative heterocycles (1.0 eq) and di-ferf-butyl dicarbonate (1eq. to 2 eq., more in particular 1.2 eq) in acetonitrile was added DMAP (0.1 to 0.5 eq. more in particular 0.1 eq). The reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with a saturated sodium bicarbonate solution. The phases were separated. The aqueous phase was extracted with dichloromethane. The organic phases were combined, washed with a saturated ammonium chloride solution, water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The BOC-protected compound was used in the next step without further purification.

Reference： [1]Patent: WO2013/45516,2013,A1 .Location in patent: Page/Page column 129; 198

8
[ 276862-85-2 ]
[ 98-59-9 ]
1-tosyl-1H-pyrrolo[3,2-b]pyridine-3-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
691 mg		To a stirred solution containing 1.50 g (12.7 mmol) of 1H-pyrrolo[3,2-b]pyridine in 20 mL of 1:1 AcOH/H2O was added 2.67 g (19.0 mmol) of hexamethylenetetramine (HMTA). The reaction mixture was heated at reflux overnight under argon. The reaction mixture was cooled to 0 C and the formed precipitate was filtered and dried under vacuum. <strong>[276862-85-2]1H-pyrrolo[3,2-b]pyridine-3-carbaldehyde</strong> (12) was obtained as a colorless solid and was used directly in the next step without further purification. To a stirred solution containing 487 mg (3.33 mmol) of <strong>[276862-85-2]1H-pyrrolo[3,2-b]pyridine-3-carbaldehyde</strong> (12) in 20 mL of anhydrous DMF at 0 C was added 119 mg (4.99 mmol) of NaH. The reaction mixture was stirred at 0 C for 10 min under argon and then 954 mg (4.99 mmol) of p-TsCl was added. The reaction mixture was stirred at 0 C under argon for 3 h, diluted with 100 mL of NaHCO3 and extracted with two 50-mL portions of EtOAc. The combined organic phase was dried (MgSO4) and concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (10 × 4 cm). Elution with 4:1 hexanes/ethyl acetate gave 1-tosyl-<strong>[276862-85-2]1H-pyrrolo[3,2-b]pyridine-3-carbaldehyde</strong> (13) as an off-white solid: yield 691 mg (23% for two steps); silica gel TLC Rf 0.35 (1:1 hexanes/ethyl acetate); 1H NMR (CDCl3, 400 MHz) d 2.31 (s, 3H), 7.23-7.29 (m, 3H), 7.77 (d, 2H, J = 8 Hz), 8.21 (d, 1H, J = 8.0 Hz), 8.38 (s, 1H), 8.62 (d, 1H, J = 4.0 Hz) and 10.29 (s, 1H); 13C NMR (CDCl3, 400 MHz) d 21.7, 120.4, 121.2, 121.4 127.3, 128.8, 130.6, 134.1, 134.8, 144.9, 146.8, 147.8 and 184.9 ; mass spectrum (APCI), m/z 301.0639 (M+H)+ (C15H13N2O3S requires m/z 301.0647).

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5924 - 5934

9
[ 276862-85-2 ]
(1-tosyl-1H-(pyrrolo[3,2-b]pyridin-3-yl))methanol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5924 - 5934

10
[ 276862-85-2 ]
3-(chloromethyl)-1-tosyl-1H-pyrrolo[3,2-b]pyridine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5924 - 5934

11
[ 276862-85-2 ]
3-(((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)methyl)-1-tosyl-1H-pyrrolo[3,2-b]pyridine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5924 - 5934

12
[ 276862-85-2 ]
methyl (S)-2-amino-3-(1-tosyl-1H-pyrrolo[3,2-b]pyridin-3-yl)propionate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5924 - 5934

13
[ 276862-85-2 ]
methyl (S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonylamino)-3-(1-tosyl-1H-pyrrolo[3,2-b]pyridin-3-yl)propionate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5924 - 5934

14
[ 276862-85-2 ]
methyl (S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonylamino)-3-(1H-pyrrolo[3,2-b]pyridin-3-yl)propionate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5924 - 5934

15
[ 276862-85-2 ]
cyanomethyl (S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonylamino)-3-(1H-pyrrolo[3,2-b]pyridin-3-yl)propionate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5924 - 5934

16
[ 276862-85-2 ]
(S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonylamino)-3-(1H-pyrrolo[3,2-b]pyridin-3-yl)propionyl-pdCpA [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5924 - 5934

17
[ 276862-85-2 ]
3-(((2S, 5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)methyl)-1H-pyrrolo[3,2-b]pyridine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5924 - 5934

18
[ 276862-85-2 ]
3-(((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)methyl)-1-methyl-1H-pyrrolo[3,2-b]pyridine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5924 - 5934

19
[ 276862-85-2 ]
methyl (S)-2-amino-3-(1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)propionate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5924 - 5934

20
[ 276862-85-2 ]
methyl (S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonylamino)-3-(1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)propionate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5924 - 5934

21
[ 276862-85-2 ]
cyanomethyl (S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonylamino)-3-(1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)propionate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5924 - 5934

22
[ 276862-85-2 ]
(S)-2-((4,5-dimethoxy-2-nitrobenzyloxy)carbonylamino)-3-(1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)propionyl-pdCpA [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5924 - 5934

23
[ 276862-85-2 ]
methyl (S)-2-acetamido-3-(1-tosyl-1H-pyrrolo[3,2-b]pyridin-3-yl)propionate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5924 - 5934

24
[ 276862-85-2 ]
methyl (S)-2-acetamido-3-(1H-pyrrolo[3,2-b]pyridin-3-yl)propionate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5924 - 5934

25
[ 276862-85-2 ]
methyl (S)-2-acetamido-3-(1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl)propionate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5924 - 5934

26
[ 276862-85-2 ]
1-(2-bromobenzenesulfonyl)-3-(piperazin-1-ylmethyl)-1H-pyrrolo[3,2-b]pyridine dihydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 1843 - 1859

27
[ 276862-85-2 ]
[ 57260-71-6 ]
C₁₇H₂₄N₄O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 1843 - 1859

28
[ 276862-85-2 ]
[ 57260-71-6 ]
C₂₃H₂₇BrN₄O₄S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 1843 - 1859

29
[ 276862-85-2 ]
6-bromo-4-methylnicotinonitrile [ No CAS ]
[ 147-85-3 ]
4-methyl-6-(3-(2-oxoethyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)nicotinonitrile [ No CAS ]