32501-05-6|1H-Pyrrolo[3,2-b]pyridin-2(3H)-one| Ambeed

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Quality Control of [ 32501-05-6 ] Purity: 95% SDS Specification

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Product Details of [ 32501-05-6 ]

CAS No. :	32501-05-6
Formula :	C₇H₆N₂O
M.W :	134.14
SMILES Code :	O=C1CC2=NC=CC=C2N1
MDL No. :	MFCD02179615
InChI Key :	IHRRHTILSRVFPW-UHFFFAOYSA-N
Pubchem ID :	316367

Safety of [ 32501-05-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 32501-05-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	39.53
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	41.99 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.04
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	-0.26
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.0
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-0.08
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.41
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.42

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.95
Solubility	15.0 mg/ml ; 0.112 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-0.16
Solubility	92.1 mg/ml ; 0.687 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.48
Solubility	0.441 mg/ml ; 0.00329 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.3 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.65

Application In Synthesis of [ 32501-05-6 ]

* 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.

Downstream synthetic route of [ 32501-05-6 ]

[ 32501-05-6 ] Synthesis Path-Downstream 1~27

1
[ 80352-63-2 ]
[ 32501-05-6 ]

References: [1]Synthetic Communications,1981,vol. 11,p. 743 - 750.

Yield	Reaction Conditions	Operation in experiment
1.82 g (66% over 3 steps)		D. 1H-Pyrrolo [3,2-b]pyridin-2(3H)-one The title C compound from the previous reaction was suspended in concentrated hydrochloric acid (120 mL) and heated to reflux for 24 hours. The reaction mixture was cooled and neutralized with solid potassium carbonate. This solution was extracted with ethyl acetate, the combined extracts dried over magnesium sulfate and the solvent removed to yield 1.82 g (66% over 3 steps) of a brown solid which was used in the next reaction without purification.

3
[ 19012-03-4 ]
[ 32501-05-6 ]
1,3-Dihydro-3-[(1-methyl-1H-indol-3-yl)methylene]-2H-pyrrolo[3,2-b]pyridin-2-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 953 - 957.

4
[ 32501-05-6 ]
3,3,5-tribromo-1,3-dihydro-pyrrolo[3,2-<i>b</i>]pyridin-2-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 953 - 957.

5
[ 295327-27-4 ]
[ 32501-05-6 ]

Yield	Reaction Conditions	Operation in experiment
62%	With hydrogenchloride; In diethyl ether;	4-Azaoxindole Ethyl 2-(3-amino-pyridin-2-yl)-acetate (6.94 g, 0.038 mol) was dissolved in diethyl ether (100 mL) at room temperature. Hydrochloric acid (2M, 35 mL) was added and the reaction was stirred for 30 minutes. The volatiles were removed to afford a brown solid that was re-crystallized from ethanol and diethyl ether (4.0 g, 62% yield). 1H NMR 400 MHz (DMSO-d6) delta12.35 (s, 1H); 8.12 (m, 1H); 7.90 (m, 1H); 7.14 (m, 1H); 5.75 (s, 2H). Electrospray MS m/z 135 (M+1).
62%	With hydrogenchloride; In diethyl ether;	d 1,3-Dihydro-2H-pyrrolo[3,2-b]pyridin-2-one Ethyl 2-(3-amino-pyridin-2-yl)-acetate (6.94 g, 0.038 mol) was dissolved in diethyl ether (100 mL) at room temperature. Hydrochloric acid (2M, 35 mL) was added, and the reaction was stirred for 30 minutes. The volatiles were removed to afford a brown solid that was recrystallized from ethanol and diethyl ether to provide the title compound (4.0 g, 62% yield). 1H NMR 400 MHz (DMSO-d6): delta12.35 (s, 1H); 8.12 (m, 1H); 7.90 (m, 1H); 7.14 (m, 1H); 5.75 (s, 2H). Electrospray MS m/a 135 (M+H).
62%	With hydrogenchloride; In diethyl ether;	d 1,3-Dihydro-2H-pyrrolo[3,2-b]pyridin-2-one Ethyl 2-(3-amino-pyridin-2-yl)-acetate (6.94 g, 0.038 mol) was dissolved in diethyl ether (100 mL) at room temperature. Hydrochloric acid (2M, 35 mL) was added, and the reaction was stirred for 30 minutes. The volatiles were removed to afford a brown solid that was recrystallized from ethanol and diethyl ether to provide the title compound (4.0 g, 62% yield). 1H NMR 400 MHz (DMSO-d6): delta 12.35 (s, 1H); 8.12 (m, 1H); 7.90 (m, 1H); 7.14 (m, 1H); 5.75 (s, 2H). Electrospray MS m/z 135 (M+H).

62%

With hydrogenchloride; In diethyl ether; water; at 20℃; for 0.5h;

d) 4-Azaoxindole ethyl 2-(3-amino-pyridin-2-yl)-acetate (6.94 g, 0.038 mol) was dissolved in diethyl ether (100 ML) at room temperature.. hydrochloric acid (2M, 35 ML) was added and the reaction was stirred for 30 minutes.. The volatiles were removed to afford a brown solid that was re-crystallized from ethanol and diethyl ether (4.0 g, 62% yield). 1H NMR 400 MHz (DMSO-d6) delta 12.35 (s, 1H); 8.12 (m, 1H); 7.90 (m, 1H); 7.14 (m, 1H); 5.75 (s, 2H).. Electrospray MS m/z 135 (M+1).

References: [1]Patent: US6369086,2002,B1 .
[2]Patent: US6369086,2002,B1 .
[3]Patent: US6624171,2003,B1 .
[4]Patent: US6350747,2002,B1 .Location in patent: Page column 72.
[5]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 953 - 957.

6
[ 5470-18-8 ]
(Z)-1-ethoxy-2-tributylstannylethene ⁽¹⁾ [ No CAS ]
[ 32501-05-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 953 - 957.

7
[ 64362-41-0 ]
[ 32501-05-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 953 - 957.

8
[ 154078-83-8 ]
[ 32501-05-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 953 - 957.

9
[ 32501-05-6 ]
5-bromo-1,3-dihydropyrrolo[3,2-b]pyridin-2-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 953 - 957.

10
[ 5470-18-8 ]
[ 32501-05-6 ]

References: [1]Synthetic Communications,1981,vol. 11,p. 743 - 750.

11
[ 80352-62-1 ]
[ 32501-05-6 ]

References: [1]Synthetic Communications,1981,vol. 11,p. 743 - 750.

12
[ 32501-05-6 ]
[ 36805-97-7 ]
[ 295327-36-5 ]

Yield	Reaction Conditions	Operation in experiment
	In DMF (N,N-dimethyl-formamide); at 20℃; for 1h;	This monomer was generated in situ (during library synthesis) from 4-aza-oxindole and dimethylformamide di-t-butylacetal in DMF.Monomer 9 and Monomer 10 were generated in situ by preparing stock solutions of the corresponding aza-oxindole. For example, 20.1 mg of 4-aza-oxindole was dissolved in 4.0 mL of ethanol. Both of the precursors for monomers 9 and 10 were transferred (0.20 ml/well) to a 96-well dry heating block (vwrBRAND Dry Block Heater, cat No.13259-066) according to the map below where M represents the monomer and A represents the amine. The ethanol was evaporated off at 50 C. until it was clear that there was no solvent remaining. DMF (0.20 mL) was added followed by the addition of dimethylformamide di-t-butylacetal (0.003 mL) and this remained at room temperature for 1 h.

References: [1]Patent: US6350747,2002,B1 .Location in patent: Page column 74, 76.

13
methyl 2-(3-nitropyridin-2-yl)acetate [ No CAS ]
[ 32501-05-6 ]

References: [1]Patent: US2003/225090,2003,A1 .Location in patent: Page 18.

14
[ 32501-05-6 ]
[ 36805-97-7 ]
3-[(dimethylamino)methylidene]-1H-pyrrolo[3,2-b]pyridin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide;	3-[(Dimethylamino)methylidene]-1H-pyrrolo[3,2-b]pyridin-2-one This monomer was generated in situ (during library synthesis) from <strong>[32501-05-6]1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one</strong> and dimethylformamide di-t-butylacetal in DMF.

References: [1]Patent: US6369086,2002,B1 .

Yield	Reaction Conditions	Operation in experiment
		Synthesis of 1,3-dihydro-4-(2-acetylthioethyl)-2-oxo-2H-pyrrolo[3,2-b]pyridinium bromide To 1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one (6.25 g, 0.05 mol) ?prepared as described in J. Org. Chem. Vol. 37, pp. 51-4, 1972! in acetonitrile (500 ml) is added S-acetyl-2-bromoethanethiol. The reaction mixture is heated at reflux for 12 hours under an atmosphere of nitrogen. The reaction mixture is the concentrated under reduced pressure and the crude residue is triturated in diethyl ether. The product can be further purified by flash chromatography with 5% isopropanol in methylene chloride on silica gel.
		Synthesis of 1,3-dihydro-4-(2-acetylthioethyl)-2-oxo-2H-pyrrolo[3,2-b]pyridinium bromide To 1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one (6.25 g, 0.05 mol) ?prepared as described in J. Org. Chem. Vol.37, pp. 51-4, 1972! in acetonitrile (500 ml) is added S-acetyl-2-bromoethanethiol. The reaction mixture is heated at reflux for 12 hours under an atmosphere of nitrogen. The reaction mixture is the concentrated under reduced pressure and the crude residue is triturated in diethyl ether. the product can be further purified by flash chromatography with 5% isopropanol in methylene chloride on silica gel.

16
tin(II)chloride dihydrate [ No CAS ]
2-(3-nitro-pyridin-2-yl)ethyl acetate [ No CAS ]
[ 32501-05-6 ]

Yield	Reaction Conditions	Operation in experiment
33%	In dichloromethane; ethyl acetate;	A mixture of 2-(3-nitro-2-pyridyl)ethyl acetate (10.1, 48 mmol), tin(II)chloride dihydrate (54.3 g, 240 mmol) and ethyl acetate was stirred and heated at reflux for 5 hours. The reaction mixture was allowed to cool overnight, filtered through diatomaceous earth and the solvent was removed by evaporation. The resulting oil was purified by flash chromatography using increasingly polar solvent mixtures starting with methylene chloride and ending with methylene chloride/methanol (10/1). Removal of the solvent by evaporation gave 4-azaoxindole (2.1 g, 33%). 1H NMR Spectrum: (DMSOd6) 3.35(br s, 2H); 7.15(m, 2H); 8.05(d, 1H); 10.50(br s, 1H) MS (ESI): [MH]+ 133

References: [1]Patent: US6294532,2001,B1 .

17
[ 87-41-2 ]
[ 32501-05-6 ]
3-(3H-isobenzofuran-1-ylidene)-1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%		EXAMPLE 73 3-(3H-Isobenzofuran-1-ylidene)-1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one To a solution of 1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one(50 mg, 0.37 mmol) in anhydrous N,N-dimethylformamide(5.0 ml) was added 1.0M LiHMDS/THF solution (0.74 ml, 0.74 mmol) under N2. After the mixture was stirred at room temperature for 10 minutes, phthalide was added (40 mg, 0.30 mmol), and then it was continuously stirred at room temperature for 4 hours. The mixture was poured into 2M HCl (4.0 ml), heated at 50 C. for 20 minutes and then poured into water (100 ml). After cooled to room temperature, the mixture was basified to pH 9 with saturated NaHCO3 solution, and was stirred at room temperature overnight. The resulting solid was filtered, washed with water, dried under vacuum and triturated with chloroform to give 3-(3H-isobenzofuran-1-ylidene)-1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one as a yellow solid (12 mg, 16%). 1H NMR (500 MHz, d6-DMSO) delta ppm 5.84 (s, 2 H) 7.05 (dd, J=7.32, 4.88 Hz, 1 H) 7.11 (dd, J=7.81, 1.46 Hz, 1 H) 7.58-7.63 (m, 1 H) 7.70-7.73 (m, 2 H) 8.13 (d, J=3.42 Hz, 1 H) 9.75 (d, J=7.81 Hz, 1 H) 10.53 (s, 1 H)

References: [1]Patent: US2008/45526,2008,A1 .Location in patent: Page/Page column 46.

18
[ 251356-80-6 ]
[ 32501-05-6 ]
[ 1350702-92-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	With piperidine; In methanol; for 5h;Reflux;	General procedure: Piperidine (0.08 mL) was added to methanol (25 mL) dissolved in substituted aldehydes 5-7 (0.18 mmol) and starting 2-indolinone derivatives 8-11 (0.18 mmol) which were prepared as described previously refPreviewPlaceHolder[6], refPreviewPlaceHolder[21], refPreviewPlaceHolder[22], refPreviewPlaceHolder[23], refPreviewPlaceHolder[24] and refPreviewPlaceHolder[25]. The mixture was refluxed for 5 h. For the targeted compounds 12-21 and 28-36, the mixture was evaporated to remove the solvent and the residue was purified by column chromatography (CH2Cl2/MeOH 100:1-10:1). For the targeted compounds 22-27, ethyl ether (15 mL) was added to the residue and the yellow precipitate was collected by filtration. The obtained precipitate was subjected to the hydrogen chloride saturated methanol to afford it as hydrochloride derivative. All the targeted compounds 12-36 show moderate to good yields under this reaction condition with the yields of 60-92%.

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 5970 - 5977.

19
[ 1350703-12-6 ]
[ 32501-05-6 ]
(Z)-N-(2-(diethylamino)ethyl)-2-oxo-6-((2-oxo-1H-pyrrolo[3,2-b]pyridin-3(2H)-ylidene)methyl)-1,2-dihydropyridine-3-carboxamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%		General procedure: Piperidine (0.08 mL) was added to methanol (25 mL) dissolved in substituted aldehydes 5-7 (0.18 mmol) and starting 2-indolinone derivatives 8-11 (0.18 mmol) which were prepared as described previously refPreviewPlaceHolder[6], refPreviewPlaceHolder[21], refPreviewPlaceHolder[22], refPreviewPlaceHolder[23], refPreviewPlaceHolder[24] and refPreviewPlaceHolder[25]. The mixture was refluxed for 5 h. For the targeted compounds 12-21 and 28-36, the mixture was evaporated to remove the solvent and the residue was purified by column chromatography (CH2Cl2/MeOH 100:1-10:1). For the targeted compounds 22-27, ethyl ether (15 mL) was added to the residue and the yellow precipitate was collected by filtration. The obtained precipitate was subjected to the hydrogen chloride saturated methanol to afford it as hydrochloride derivative. All the targeted compounds 12-36 show moderate to good yields under this reaction condition with the yields of 60-92%.

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 5970 - 5977.

20
[ 2338-71-8 ]
[ 32501-05-6 ]
(E)-3-((5-fluoro-1H-indol-3-yl)methylene)-1H-pyrrolo[3,2-b]pyridin-2(3H)-one [ No CAS ]
(Z)-3-((5-fluoro-1H-indol-3-yl)methylene)-1H-pyrrolo[3,2-b]pyridin-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine; In methanol; for 5h;Reflux;	General procedure: Piperidine (0.08 mL) was added to methanol (25 mL) dissolved in substituted aldehydes 5-7 (0.18 mmol) and starting 2-indolinone derivatives 8-11 (0.18 mmol) which were prepared as described previously refPreviewPlaceHolder[6], refPreviewPlaceHolder[21], refPreviewPlaceHolder[22], refPreviewPlaceHolder[23], refPreviewPlaceHolder[24] and refPreviewPlaceHolder[25]. The mixture was refluxed for 5 h. For the targeted compounds 12-21 and 28-36, the mixture was evaporated to remove the solvent and the residue was purified by column chromatography (CH2Cl2/MeOH 100:1-10:1). For the targeted compounds 22-27, ethyl ether (15 mL) was added to the residue and the yellow precipitate was collected by filtration. The obtained precipitate was subjected to the hydrogen chloride saturated methanol to afford it as hydrochloride derivative. All the targeted compounds 12-36 show moderate to good yields under this reaction condition with the yields of 60-92%.

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 5970 - 5977.

21
[ 2795-41-7 ]
[ 32501-05-6 ]
(E)-3-((6-fluoro-1H-indol-3-yl)methylene)-1H-pyrrolo[3,2-b]pyridin-2(3H)-one [ No CAS ]
(Z)-3-((6-fluoro-1H-indol-3-yl)methylene)-1H-pyrrolo[3,2-b]pyridin-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine; In methanol; for 5h;Reflux;	General procedure: Piperidine (0.08 mL) was added to methanol (25 mL) dissolved in substituted aldehydes 5-7 (0.18 mmol) and starting 2-indolinone derivatives 8-11 (0.18 mmol) which were prepared as described previously refPreviewPlaceHolder[6], refPreviewPlaceHolder[21], refPreviewPlaceHolder[22], refPreviewPlaceHolder[23], refPreviewPlaceHolder[24] and refPreviewPlaceHolder[25]. The mixture was refluxed for 5 h. For the targeted compounds 12-21 and 28-36, the mixture was evaporated to remove the solvent and the residue was purified by column chromatography (CH2Cl2/MeOH 100:1-10:1). For the targeted compounds 22-27, ethyl ether (15 mL) was added to the residue and the yellow precipitate was collected by filtration. The obtained precipitate was subjected to the hydrogen chloride saturated methanol to afford it as hydrochloride derivative. All the targeted compounds 12-36 show moderate to good yields under this reaction condition with the yields of 60-92%.

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 5970 - 5977.

22
7-ethyl-1H-indole-3-carbaldehyde [ No CAS ]
[ 32501-05-6 ]
(E)-3-((7-ethyl-1H-indol-3-yl)methylene)-1H-pyrrolo[3,-2-b]pyridin-2(3H)-one [ No CAS ]
(Z)-3-((7-ethyl-1H-indol-3-yl)methylene)-1H-pyrrolo[3,-2-b]pyridin-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine; In methanol; for 5h;Reflux;	General procedure: Piperidine (0.08 mL) was added to methanol (25 mL) dissolved in substituted aldehydes 5-7 (0.18 mmol) and starting 2-indolinone derivatives 8-11 (0.18 mmol) which were prepared as described previously refPreviewPlaceHolder[6], refPreviewPlaceHolder[21], refPreviewPlaceHolder[22], refPreviewPlaceHolder[23], refPreviewPlaceHolder[24] and refPreviewPlaceHolder[25]. The mixture was refluxed for 5 h. For the targeted compounds 12-21 and 28-36, the mixture was evaporated to remove the solvent and the residue was purified by column chromatography (CH2Cl2/MeOH 100:1-10:1). For the targeted compounds 22-27, ethyl ether (15 mL) was added to the residue and the yellow precipitate was collected by filtration. The obtained precipitate was subjected to the hydrogen chloride saturated methanol to afford it as hydrochloride derivative. All the targeted compounds 12-36 show moderate to good yields under this reaction condition with the yields of 60-92%.

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 5970 - 5977.

23
[ 32501-05-6 ]
methyl rac-4-((2S,3S,4S,5R)-4-(3-chloro-2-fluorophenyl)-2-neopentyl-2'-oxo-1',2'-dihydrospiro[pyrrolidine-3,3'-pyrrolo[3,2-b]pyridine]-5-ylcarboxamido)-3-methoxybenzoate [ No CAS ]

References: [1]Patent: US2012/46306,2012,A1 .

24
[ 32501-05-6 ]
rac-4-((2S,3S,4S,5R)-4-(3-chloro-2-fluorophenyl)-2-neopentyl-2'-oxo-1',2'-dihydrospiro[pyrrolidine-3,3'-pyrrolo[3,2-b]pyridine]-5-ylcarboxamido)-3-methoxybenzoic acid [ No CAS ]

References: [1]Patent: US2012/46306,2012,A1 .

25
[ 85070-48-0 ]
[ 32501-05-6 ]
[ 1360821-93-7 ]

Yield	Reaction Conditions	Operation in experiment
64%	With piperidine; In methanol; at 50℃;	Example 20 Preparation of intermediate E/Z-3-(3-Chloro-2-fluoro-benzylidene)-1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one To a suspension of <strong>[32501-05-6]1H-pyrrolo[3,2-b]pyridin-2(3H)-one</strong> (Sinova. 933 mg, 6.96 mmol) in MeOH (35 mL) was added 3-chloro-2-fluorobenzaldehyde (Oakwood, 3.58 g, 22.6 mmol) giving a clear solution. Piperidine (Lancaster, 2.58 g, 30.30 mmol) was added slowly. After stirred for a few minutes, the reaction mixture was heated at 50 C. for 3 h, resulting in a yellow precipitation. The reaction mixture was cooled and the precipitate was filtered, washed with cold MeOH and dried in vacuum to give E/Z-3-(3-chloro-2-fluoro-benzylidene)-1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one as a light yellow crystalline solid (1.22 g, 64%). MS (ES+) m/z [(M+H)+]: 275

References: [1]Patent: US2012/46306,2012,A1 .Location in patent: Page/Page column 19.

26
diethyl 2,2'-[carbonylbis(iminopyridine-3,2-diyl)]diacetate [ No CAS ]
C₂₇H₂₆N₆O₇ [ No CAS ]
[ 32501-05-6 ]

Yield	Reaction Conditions	Operation in experiment
44%; 36%	With potassium carbonate; In acetonitrile; at 60℃; for 3h;	To a solution of urea derivative 16 (340 mg, 0.88 mmol) in acetonitrile (20 mL) at 60 C was added excess K2CO3 (0.6 g, 4.3 mmol). After stirring for 3 h, excess K2CO3 was filtered and solvent was evaporated under reduced pressure. The formed products were separated by column chromatography (silica gel, EtOAc/hexane, 99:1). The fragmentation product 19 (43 mg, 36%) was isolated as the first fraction. The major product 18 was eluted as the second fraction (210 mg, 44%). 4.5.1 1H-Pyrrolo[3,2-b]pyridin-2(3H)-one (19)21 Colorless viscous liquid. 1H NMR (400 MHz, CDCl3) delta 9.15 (br s, 1H), 8.14 (dd, J=2.4, 4.4 Hz, 1H), 7.08 (br s, 1H), 7.07 (br s, 1H), 3.62 (s, 2H). 13C NMR (100 MHz, CDCl3) delta 175.6, 148.0, 143.1, 137.6, 122.7, 115.9, 37.8. 4.5.2 Diethyl 2,2?-(3,3?-((2-hydroxy-1H-pyrrolo[3,2-b]pyridine-1,3-dicarbonyl) bis (azanediyl)) bis(pyridine-3,2-diyl))diacetate (18). White crystals from EtOAc, mp 186-187 C. 1H NMR (400 MHz, CDCl3) delta 12.52 (s, 1H), 11.28 (s, 1H), 9.71 (s, 1H), 8.43 (dd, J=7.7, 0.9 Hz, 1H), 8.32 (dd, J=4.6, 1.4 Hz, 1H), 8.30 (dd, J=4.7, 1.4 Hz, 1H), 8.26 (dd, J=8.2, 1.5 Hz, 1H), 8.22 (dd, J=8.2, 1.4 Hz, 1H), 7.22 (dd, J=8.2, 4.7 Hz, 1H), 7.15 (dd, J=8.1, 4.7 Hz, 2H), 6.73 (dd, J=7.7, 6.6 Hz, 1H), 4.18 (q, J=7.1 Hz, 2H), 4.14 (q, J=7.1 Hz, 2H), 3.97 (s, 2H), 3.94 (s, 2H), 1.20 (t, J=7.1 Hz, 3H), 1.16 (t, J=7.1 Hz, 3H). 13C NMR (100 MHz, CDCl3) delta 170.0 (2C), 166.2, 163.9, 150.6, 147.3, 146.0, 145.5, 145.4, 143.3, 138.9, 133.1, 132.7, 131.5, 130.8, 128.6, 122.8, 122.7, 122.7, 113.4, 85.3, 61.3 (2C), 40.7, 40.6, 14.1. numax (ATR): 3284, 2983, 1721, 1634, 1594, 1544, 1429, 1397, 1329, 1283, 1216, 1140, 1024. HRMS: m/z [M+Na]+ calcd for C27H26N6O7: 545.17847; found: 545.17686

References: [1]Tetrahedron,2015,vol. 71,p. 252 - 258.

27
ethyl 2-(3-(3-phenylureido)pyridin-2-yl)acetate [ No CAS ]
2-hydroxy-N¹,N³-diphenyl-1H-pyrrolo[3,2-b]pyridine-1,3-dicarboxamide [ No CAS ]
[ 32501-05-6 ]

Yield	Reaction Conditions	Operation in experiment
34%; 26%	With potassium carbonate; In acetonitrile; at 60℃;	To a solution of urea derivative 24 (780 mg, 2.61 mmol) in acetonitrile (20 mL) at 60 C was added excess K2CO3 (1.5 g, 0.01 mol). After stirring for 2 h, excess K2CO3 was filtered and solvent was evaporated under reduced pressure. The residue was treated with chloroform, pyrrolo-prydinone 19 was soluble in chloroform and whereas the major product 25 was insoluble. Analytical pure samples were obtained by column chromatography on silica gel eluting with EtOAc/n-hexane (8:2) to give 19 (90 mg, 26%). The major compound 25 was purified by washing with cold methanol (333 mg, 34%). 4.7.1. 2-Hydroxy-N1,N3-diphenyl-1H-pyrrolo[3,2-b]pyridine-1,3-dicarboxamide (25). Brown solid, mp 194-195 C. 1H NMR (400 MHz, DMSO) delta 12.64 (s, 1H), 11.28 (s, 1H), 8.26 (dd, J=7.8, 1.4 Hz, 1H), 8.14 (dd, J=5.1, 1.4 Hz, 1H), 7.75 (d, J=7.6 Hz, 2H), 7.69 (d, J=7.6 Hz, 2H), 7.43 (t, J=7.9 Hz, 2H), 7.34 (t, J=7.9 Hz, 2H), 7.15 (t, J=7.4 Hz, 1H), 7.01 (t, J=7.3 Hz, 1H), 6.87 (dd, J=7.8, 5.1 Hz, 1H). 13C NMR (100 MHz, DMSO) delta 165.4, 163.2, 151.4, 147.8, 141.0, 140.7, 138.4, 129.0, 128.7, 124.4, 123.0, 121.3, 119.4, 118.5, 118.3, 113.2, 85.1. numax (ATR): 3219, 3026, 1694, 1590, 1547, 1498, 1455, 1378, 1310, 1249, 1180, 1077. HRMS: m/z [M+Na]+ calcd for C21H16N4O3: 371.11496; found: 371.11158.

References: [1]Tetrahedron,2015,vol. 71,p. 252 - 258.

Historical Records

Technical Information

• Acyl Group Substitution • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Hydride Reductions • Lawesson's Reagent • Preparation of Amines • Reactions of Amines • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes

Related Functional Groups of
[ 32501-05-6 ]

Amides

A428556 [56057-25-1]

7-Methyl-1H-pyrrolo[3,2-b]pyridin-2(3H)-one

Similarity: 0.94

A257660 [1190319-62-0]

6-Bromo-1H-pyrrolo[3,2-b]pyridin-2(3H)-one

Similarity: 0.86

A121242 [178393-14-1]

5-Methoxy-1H-pyrrolo[3,2-b]pyridin-2(3H)-one

Similarity: 0.82

A105753 [295327-22-9]

1H-Pyrrolo[2,3-c]pyridin-2(3H)-one hydrochloride

Similarity: 0.76

A146320 [70298-88-3]

2,2-Dimehtyl-N-pyridin-3-yl-propionamide

Similarity: 0.75

Related Parent Nucleus of
[ 32501-05-6 ]

Other Aromatic Heterocycles

A428556 [56057-25-1]

7-Methyl-1H-pyrrolo[3,2-b]pyridin-2(3H)-one

Similarity: 0.94

A257660 [1190319-62-0]

6-Bromo-1H-pyrrolo[3,2-b]pyridin-2(3H)-one

Similarity: 0.86

A121242 [178393-14-1]

5-Methoxy-1H-pyrrolo[3,2-b]pyridin-2(3H)-one

Similarity: 0.82

A115139 [13993-61-8]

1,2,3,4-Tetrahydro-1,5-naphthyridine

Similarity: 0.77

A178433 [276862-85-2]

1H-Pyrrolo[3,2-b]pyridine-3-carbaldehyde

Similarity: 0.76

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CAS No.: 32501-05-6

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