5654-97-7|1,3-Dihydro-2H-pyrrolo[2,3-b]pyridin-2-one| Ambeed

Structure of 5654-97-7

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Quality Control of [ 5654-97-7 ] Purity: 97% SDS Specification

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Product Details of [ 5654-97-7 ]

CAS No. :	5654-97-7
Formula :	C₇H₆N₂O
M.W :	134.14
SMILES Code :	N2C1=NC=CC=C1CC2=O
MDL No. :	MFCD07367951
InChI Key :	ZXSQEZNORDWBGZ-UHFFFAOYSA-N
Pubchem ID :	13864095

Safety of [ 5654-97-7 ]

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

Computational Chemistry of [ 5654-97-7 ] 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.	1.13
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	0.03
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	0.5

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.13
Solubility	9.84 mg/ml ; 0.0734 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.	-0.46
Solubility	46.1 mg/ml ; 0.343 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.	-7.1 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)	1.56

Application In Synthesis of [ 5654-97-7 ]

* 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 [ 5654-97-7 ]

[ 5654-97-7 ] Synthesis Path-Downstream 1~35

1
[ 5654-97-7 ]
[ 126807-18-9 ]

References: [1]Helvetica Chimica Acta,1941,vol. 24,p. 141E,145E,150E.

2
[ 101860-97-3 ]
[ 5654-97-7 ]

Yield	Reaction Conditions	Operation in experiment
31%	toluene-4-sulfonic acid; In pentan-1-ol; for 48h;Reflux;	The mother liquor of the foregoing example was extracted three times with an equal volume of ethyl acetate and the combined organic phases were dried over sodium sulphate. Removal of the solvent afforded the product as colourless solid. A suspension of 2-amino-3-pyridineacetic acid (2.0 g, 12.0 mmol) and a catalytic amount of p-toluenesulfonic acid in amyl alcohol was refluxed for 48 h. After removal of the solvent from the clear solution, the residue was purified by column chromatography on silica gel using ethyl acetate : hexane (3:1) as eluent to provide a solid (0.5 g, 3.7 mmol, 31 %). 1H-NMR (400 MHz, DMSO-d6, delta = 2.49 ppm): 10.96 (s, 1H, NH), 8.02 (d, 1H, 3JH,H = 5.3 Hz, 6-CH), 7.52 (d, 1H, 3JH,H = 7.0 Hz, 4-CH), 6.91 (dd, 1H, 3JH,H = 7.0 Hz, 4JH,H = 5.3Hz, 5-CH), 3.53 (s, 2H, CH2). 13C-{1H}-NMR (150 MHz, DMSO-d6, delta = 39.5 ppm): 1765.8 (C2), 1508.2 (C7a), 146.1 (C6), 131.8 (C4), 120.4 (C3a), 117.3 (C5), 35.2 (C3).

References: [1]Patent: EP2199292,2010,A1 .Location in patent: Page/Page column 10.
[2]Journal of the American Chemical Society,1959,vol. 81,p. 740,742.
[3]Journal of Medicinal Chemistry,1990,vol. 33,p. 2697 - 2706.
[4]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 247 - 255.

3
[ 121-69-7 ]
[ 438210-61-8 ]
[ 5654-97-7 ]

References: [1]Helvetica Chimica Acta,1941,vol. 24,p. 1471,1479.

4
[ 5654-97-7 ]
[ 74-88-4 ]
[ 109535-73-1 ]

Yield	Reaction Conditions	Operation in experiment
		Step 3: 3,3-Dimethyl-1 ,3-dihydro-pyrrolo[2,3-b]pyridin-2-one1 ,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (500mg, 3.73mmol) in dry THF (40 ml) under at atmosphere of nitrogen was treated with N1 ,N1 ,N2,N2-tetramethylethane-1 ,2- diamine (1.956 ml, 13.05 mmol). The mixture was cooled to -78C in an acetone/dry ice bath. n-BuLi (1.6M in Hexanes) (8.15 ml, 13.05 mmol) was added dropwise over 30mins. After addition, the mixture was stirred for a further 30 mins and then treated dropwise with methyl iodide (0.816 ml, 13.05 mmol) and stirred at RT overnight. The reaction was quenched by careful addition of NH4CI (20 ml) and the mixture was extracted with EtOAc (2 x75 ml). The organic portion was separated and washed with sat NaHC03, brine, dried (MgS04) and concentrated in vacuo to give a pale yellow powder. The methylation process was repeated twice to obtain the dimethylated product. Purification of the resulting solid by chromatography on silica eluting with 0% to 50% EtOAc in iso-hexane afforded the title product; H NMR (400 MHz, DMSO-d6) delta 10.95 (1 H, s), 8.05 (1 H, dd), 7.65 (1 H, dd), 6.95 (1 H, dd), 1.25 (6H, s).
0.1 g		To a stirred solution of 7-Azaoxindole 1 (0.5 g ,3.73mmol ) in anhydrous THF(10 ml ) was added «-BuLi (0.47g,7.42 mmol)at -78 C followed by TMEDA(0.865 g, 7.42mmol ). After lh Mel( 0.876 g, 7.42 mmol) was added slowly and mixture was allowed to come up to room temperature. After stirring for lh , saturated aqueous ammonium chloride was added and the crude material was partitioned between water and ethyl acetate. Organic layer was separated, dried over sodium sulphate and concentrated under vacuum. Crude compound was purified by column chromatography by eluting with 40% ethyl acetate in pet ether to get the desired compound 2 (0.1 g)
0.1 g		Step-1 [0050] To a stirred solution of 7-Azaoxindole 1 (0.5 g, 3.73 mmol) in anhydrous THF (10 ml) was added n-BuLi (0.47 g, 7.42 mmol) at -78 C. followed by TMEDA (0.865 g, 7.42 mmol). After 1 h MeI (0.876 g, 7.42 mmol) was added slowly and mixture was allowed to come up to room temperature. After stirring for 1 h, saturated aqueous ammonium chloride was added and the crude material was partitioned between water and ethyl acetate. Organic layer was separated, dried over sodium sulphate and concentrated under vacuum. Crude compound was purified by column chromatography by eluting with 40% ethyl acetate in pet ether to get the desired compound 2 (0.1 g)

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2697 - 2706.
[2]Patent: WO2011/92293,A1 .Location in patent: Page/Page column 84.
Patent: ,2011, .Location in patent: Page/Page column 84.
[3]Patent: WO2013/42035,2013,A1 .Location in patent: Page/Page column 13.
[4]Patent: US2014/249170,2014,A1 .Location in patent: Paragraph 0049; 0050.

5
[ 113423-51-1 ]
[ 5654-97-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	With acetic acid; zinc; In acetonitrile;	7-Azaoxindole 3,3-Dibromo-7-azaoxindole (2.9 g) was dissolved in a mixture of 20 mL of acetic acid and 30 mL of acetonitrile. To the solution was added 6.5 g of zinc dust. The mixture was stirred for 2 hrs at room temperature. The solid was filtered from the mixture and the solvent evaporated. The residue was slurried with ethyl acetate. The ethyl acetate solution containing insoluble solid was passed through a short column of silica gel. The collected ethyl acetate solution was evaporated and the residue dried under vacuum to give 1.8 g (yield 91%) of 7-azaoxindole acetic acid salt.
91%	With acetic acid; zinc; In acetonitrile;	7-Azaoxindole 3,3-Dibromo-7-azaoxindole (2.9 g) was dissolved in a mixture of 20 mL of acetic acid and 30 mL of acetonitrile. To the solution was added 6.5 g of zinc dust. The mixture was stirred for 2 hrs at room temperature. The solid was filtered from the mixture and the solvent evaporated. The residue was slurried with ethyl acetate. The ethyl acetate solution containing insoluble solid was passed through a short column of silica gel. The collected ethyl acetate solution was evaporated and the residue dried under vacuum to give 1.8 g (yield 91%) of 7-azaoxindole acetic acid salt.
91%	With acetic acid; zinc; In acetonitrile; at 20℃; for 2h;	7-Azaoxindole 3,3-Dibromo-7-azaoxindole (2.9 g) was dissolved in a mixture of 20 ML of acetic acid and 30 ML of acetonitrile.. To the solution was added 6.5 g of zinc dust.. The mixture was stirred for 2 hrs at room temperature.. The solid was filtered from the mixture and the solvent evaporated.. The residue was slurried with ethyl acetate.. The ethyl acetate solution containing insoluble solid was passed through a short column of silica gel.. The collected ethyl acetate solution was evaporated and the residue dried under vacuum to give 1.8 g (yield 91%) of 7-azaoxindole acetic acid salt.

76%		General procedure: To a stirred solution of azaindole (10a or 10b, 12.7 mmol) in tert-butyl alcohol (100 mL) and H2O (100 mL) at room temperature, Br2 (2.6 mL, 50.5 mmol) was added dropwise over 20 min. The mixture was stirred for 1 h and the yellow precipitate (10b, or 11b) was collected by filtration. The dried precipitate (10b, or 11b, 4.8 mmol) was refluxed with 5% Pd-C (1.0 g) in 60 mL of 8.8% HCOOH/CH3OH for 12 h under nitrogen. The catalyst was removed by filtration through a pad of celite. After removal of the solvent, the residual was adjusted to pH 8-9 by addition of saturated K2CO3 solution. The solution was stored in the refrigerator overnight and the precipitate was filtered to give 5-azaindolin-2-one (10) or 7-azaindolin-2-one (11).
70%	With ammonium chloride; zinc; In tetrahydrofuran; water; at 20℃; for 2h;	b) 7-Azaoxindole A solution of 3,3-dibromo-7-azaoxindole (2.0 g, 7.2 mmol) in THF (50 ML) is stirred at room temperature and a saturated aqueous solution of NH4Cl is added.. Activated zinc powder is added and the reaction mixture is stirred for 2 h.. The zinc is removed by filtration through a pad of diatomaceous earth and the organic layer is separated.. The aqueous layer is extracted with THF (10 ML) and the combined organic layers are dried over anhydrous MgSO4, filtered and evaporated.. The residue is slurried in 10:1 CHCl3:MeOH (15 ML) and filtered through a pad of silica gel and the filtrate is evaporated.. The residue is triturated with water and the solid is collected by filtration and dried under vacuum to give 7-azaoxindole, 0.668 g (70%). 1H NMR (DMSO-d6) delta 10.94 (s, 1H), 8.02 (d, 1H, J=5.2 Hz), 7.52 (d, 1H, J=6.8 Hz), 6.90 (dd, 1H, J=6.8, 5.2 Hz), 3.53 (s, 2H). MS(AP-ve) 133 (100) (M-H)
		Step 2: 1 ,3-Dihydro-pyrrolo[2,3-b]pyridin-2-oneTo a solution of 3,3-dibromo-1 ,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (4.6 g, 15.76 mmol) in AcOH (80 ml) under N2 was added zinc powder (10.30 g, 10 eq). The mixture was stirred at RT for 30 min under N2 and then filtered through Celite (filter material) to remove the Zn. AcOH was removed in vacuo and the mixture was diluted with EtOAc and washed with NaHC03. The organic phase was separated dried(MgS04) and concentrated in vacuo to afford the title product; 1H NMR (400 MHz, DMSO-d6) delta 10.95 (1 H, s), 8.05(1 H, d), 7.55 (1 H, d), 6.95 (1 H, t), 3.55 (2H, s).

References: [1]Patent: US2003/69421,2003,A1 .
[2]Patent: US6486185,2002,B1 .
[3]Patent: US6350754,2002,B2 .Location in patent: Page column 26.
[4]European Journal of Medicinal Chemistry,2011,vol. 46,p. 5970 - 5977.
[5]Tetrahedron Letters,1987,vol. 28,p. 4027 - 4030.
[6]Tetrahedron Letters,1987,vol. 28,p. 4027 - 4030.
[7]Patent: US6350747,2002,B1 .Location in patent: Page column 71.
[8]Patent: WO2011/92293,A1 .Location in patent: Page/Page column 84.
Patent: ,2011, .Location in patent: Page/Page column 84.
[9]Dyes and Pigments,2020,vol. 180.

6
[ 205323-23-5 ]
[ 5654-97-7 ]

References: [1]Journal of Heterocyclic Chemistry,1998,vol. 35,p. 145 - 149.

8
[ 121-69-7 ]
1-<2-amino-<3>pyridyl>-2-diazo-ethanol [ No CAS ]
[ 5654-97-7 ]

References: [1]Helvetica Chimica Acta,1941,vol. 24,p. 141E,145E,150E.

9
[ 5654-97-7 ]
[ 19012-03-4 ]
3-(1-methyl-1H-indol-3-ylmethylene)-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate; In ethanol; at 20℃;	General procedure: Various aldehydes (1.0 equiv) were added to stirred solutions of indolin-2-one, 5-chloroindolin-2-one or <strong>[5654-97-7]7-azaoxindole</strong> (1.0equiv) in absolute ethanol. After stirring at room temperature for 5 min NaOEt/EtOH (0.5 mL) was added and the mixture was then stirred at room temperature overnight. The solvent was then removed under vacuum. The residue was washed with saturated sodium chloride solution and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under vacuum. The solid part was purified by chromatography over silica gel using ethyl acetate/petroleum ether as the eluent to afford desired compounds 1a-1g, 2a, 3a.

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 953 - 957.
[2]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 6953 - 6960.

10
[ 5654-97-7 ]
[ 957122-50-8 ]
[ 957122-52-0 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hydroxide; water; In tetrahydrofuran; for 0.333333h;	To a solution of 4,5-bis(bromomethyl)pyridine-2-carbonitrile from Step B (2.56 g, 8.83 mmol) and <strong>[5654-97-7]1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one</strong> [Marfat & Carta (1987) Tetrahedron Lett. 28, 4027] (1.18 g, 8.83 mmol) in THF (120 mL) and H2O (60 mL) was added lithium hydroxide monohydrate (1.11 g, 26.5 mmol). After 20 min, the reaction mixture was poured onto water (100 mL) and extracted with EtOAc (3×100 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH:NH4OH-100:0:0 to 95:5:1, to give the title compound. MS: m/z=263 (M+1).
	With lithium hydroxide; In tetrahydrofuran; water; for 0.333333h;	To a solution of 4,5-&/s(bromomethyl)pyridine-2-carbonitrile from Step B (2.56 g, 8.83 mmol) and l,3-dihydro-2H-pyrrolo[2,3-]pyridin-2-one [Marfat & Carta (1987) Tetrahedron Lett. 28, 4027] (1.18 g, 8.83 mmol) in THF (120 mL) and H2O (60 mL) was added lithium hydroxide monohydrate (1.1 1 g, 26.5 mmol). After 20 min, the reaction mixture was poured onto water (100 mL) and extracted with EtOAc (3 x 100 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl^MeOH: NH4OH - 100:0:0 to 95:5:1, to give the title compound. MS: mlz = 263 (M + 1).
	With lithium hydroxide; In tetrahydrofuran; water; for 0.333333h;	Step C. (+/-)-2'-Oxo-l2'.5,7-tetrahydrospiro[cyclopenta['c1pyridine-6.3'-pyrrolo[2.3-lpyridinel-3- carbonitrileTo a solution of 4,5-£/.s(bromomethyl)pyridine-2-carbonitrile from Step B (2.56 g, 8.83 mmol) and l,3-dihydro-2H-pyrrolo[2,3-Z>]pyridin-2-one [Marfat & Carta (1987) Tetrahedron Lett. 28, 4027] (1.18 g, 8.83 mmol) in TFfF (120 mL) and H2O (60 mL) was added lithium hydroxide monohydrate (1.11 g, 26.5 mmol). After 20 min, the reaction mixture was poured onto water (100 mL) and extracted with EtOAc (3 x 100 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH: NH4OH - 100:0:0 to 95:5: 1, to give the title compound. MS: m/z = 263 (M + l).

	With lithium hydroxide monohydrate; water; In tetrahydrofuran; for 0.333333h;	Step C. (+/-)-2'-Oxo-l25J-tetrahvdrospiro[cyclopenta[c]pyridine-6,3'-pyrrolo[23-6]rhoyridine]- 3-carbonitrileTo a solution of 4,5-6 J5(bromomethyi)pyridine-2-carbonitrile from Step B (2.56 g, 8.83 mmol) and 1 ,3-dihydro-2H-pyrrolo[2,3-^3pyridin-2-one (Marfat & Carta, Tetrahedron Lett. , 1987, 28, 4027) (1.18 g, 8.83 mmol) in TEtaF (120 mL) and Eta2O (60 mL) was added lithium hydroxide monohydrate (1.11 g, 26.5 mmol). After 20 min, the reaction mixture was poured onto water (100 mL) and extracted with EtOAc (3 * 100 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CEt°Ct°-.MeOH: NH4OH from 100:0:0 to 95:5:1, to give the title compound. MS: mlz = 263 (M + 1).
	With lithium hydroxide; water; In tetrahydrofuran; for 0.333333h;	To a solution of 4,5-«(bromomethyl)pyridine-2-carbonitrile from Step B (2.56 g, 8.83 mmol) and l,3-dihydro-2H-pyrrolo[2,3-Z>]pyridin-2-one (1.18 g, 8.83 mmol, Marfat et al (1987) Tetrahedron Lett. 28, 4027) in THF (120 mL) and H2O (60 mL) was added lithium hydroxide monohydrate (1.11 g, 26.5 mmol). After 20 min, the reaction mixture was poured onto water (100 mL) and extracted with EtOAc (3 x 100 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2: MeOH: NH4OH - 100:0:0 to 95:5:1, to give the title compound. MS: mlz = 263 (M + 1).
	With lithium hydroxide; In tetrahydrofuran; water; for 0.333333h;	Step C. (+--2'-Oxo-r,2',5J-tetrahvdrospirorcvclopentarc1pyridine-6,3'-pyrrolor2,3-?1pyridine1- 3-carbonitrileTo a solution of 4,5-/ro(bromomethyl)pyridine-2-carbonitrile from Step B (2.5610 g, 8.83 mmol) and l,3-dihydro-2H-pyrrolo[2,3-6]pyridin-2-one [Marfat & Carta (1987)Tetrahedron Lett. 28, 4027] (1.18 g, 8.83 mmol) in T?F (120 mL) and ?2O (60 mL) was added lithium hydroxide monohydrate (1.11 g, 26.5 mmol). After 20 min, the reaction mixture was poured onto water (100 mL) and extracted with EtOAc (3 x 100 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was15 purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH: NH4OH - 100:0:0 to 95:5: 1, to give the title compound. MS: mlz = 263 (M + 1).

References: [1]Patent: US2007/265225,2007,A1 .Location in patent: Page/Page column 60.
[2]Patent: WO2008/130524,2008,A1 .Location in patent: Page/Page column 41; 46.
[3]Patent: WO2008/130512,2008,A1 .Location in patent: Page/Page column 54.
[4]Patent: WO2010/77752,2010,A1 .Location in patent: Page/Page column 76.
[5]Patent: WO2008/112159,2008,A2 .Location in patent: Page/Page column 82.
[6]Patent: WO2009/120652,2009,A2 .Location in patent: Page/Page column 82.

11
[ 956460-94-9 ]
[ 5654-97-7 ]
[ 956460-93-8 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; zinc; In methanol; at 20℃; for 3h;	4B. 4-Fluoro-l,3-dihvdro-pyrrolor2,3-blpyridin-2-oneA mixture of 3,3-dibromo-4-fluoro-l,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (312mg, l.Ommol), acetic acid (4.5ml), zinc dust (658mg, lOmmol) and methanol (4.5ml) was stirred at room temperature for 3 hours. Brine was added and the reaction was extracted with ethyl acetate. The organic liquors were washed with brine, dried (MgSO4) and concentrated to furnish the title compound (184mg, contains -40% des-fluorinated product). Used thus in further reactions.
	With acetic acid; zinc; In methanol; at 20℃; for 3h;	E2. 4-Fluoro-l,3-dihvdro-pyrrolor2,3-blpyridin-2-one; A mixture of 3,3-dibromo-4-fluoro-l,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (312mg, l.Ommol), acetic acid (4.5ml), zinc dust (658mg, lOmmol) and methanol (4.5ml) was stirred at room temperature for 3 hours. Brine was added and the reaction was extracted with ethyl acetate. The organic liquors were washed with brine, dried (MgSO4) and concentrated to furnish the title compound (184mg, contains -40% des-fluorinated product). Used thus in further reactions.
	With acetic acid; zinc; In methanol; at 20℃; for 3h;	E2. 4-Fluoro-l ,3-dihydro-pyrrolo[2,3-blpyridin-2-oneA mixture of 3,3-dibromo-4-fluoro-l,3-dihydro-pyrrolo[2,3-b]pyridin-2-one(312mg, l.Ommol), acetic acid (4.5ml), zinc dust (658mg, lOmmol) and methanol (4.5ml) was stirred at room temperature for 3 hours. Brine was added and the reaction was extracted with ethyl acetate. The organic liquors were washed with brine, dried (MgSO4) and concentrated to furnish the title compound (184mg, contains -40% des-fluorinated product). Used thus in further reactions.

References: [1]Patent: WO2008/75109,2008,A1 .Location in patent: Page/Page column 114.
[2]Patent: WO2008/75110,2008,A1 .Location in patent: Page/Page column 104-105.
[3]Patent: WO2007/125325,2007,A1 .Location in patent: Page/Page column 124.

12
[ 500-22-1 ]
[ 5654-97-7 ]

References: [1]Journal of Heterocyclic Chemistry,1998,vol. 35,p. 145 - 149.

13
[ 138625-36-2 ]
[ 5654-97-7 ]

References: [1]Journal of Heterocyclic Chemistry,1998,vol. 35,p. 145 - 149.

14
[ 155705-86-5 ]
[ 5654-97-7 ]

References: [1]Journal of Heterocyclic Chemistry,1998,vol. 35,p. 145 - 149.

15
[ 155705-76-3 ]
[ 5654-97-7 ]

References: [1]Journal of Heterocyclic Chemistry,1998,vol. 35,p. 145 - 149.

16
[ 155705-77-4 ]
[ 5654-97-7 ]

References: [1]Journal of Heterocyclic Chemistry,1998,vol. 35,p. 145 - 149.

17
[ 205323-19-9 ]
[ 5654-97-7 ]

References: [1]Journal of Heterocyclic Chemistry,1998,vol. 35,p. 145 - 149.

18
[ 271-63-6 ]
[ 5654-97-7 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 4027 - 4030.
[2]European Journal of Medicinal Chemistry,2011,vol. 46,p. 5970 - 5977.
[3]ChemMedChem,2012,vol. 7,p. 777 - 791.
[4]Patent: WO2011/92293,A1 .
Patent: ,2011, .
[5]Dyes and Pigments,2020,vol. 180.

19
[ 1603-40-3 ]
[ 5654-97-7 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2697 - 2706.
[2]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 247 - 255.
[3]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 247 - 255.

20
[ 86847-66-7 ]
[ 5654-97-7 ]

21
[ 1071087-00-7 ]
[ 5654-97-7 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2697 - 2706.
[2]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 247 - 255.

22
[ 5654-97-7 ]
[ 5654-95-5 ]

Yield	Reaction Conditions	Operation in experiment
65%	With N-Bromosuccinimide; dimethyl sulfoxide; at 120℃; for 0.5h;	Dried DMSO (6 mL) was heated to 120 C and a solution of 8 (500 mg, 3.7 mmol) and N-bromosuccinimide (690.6 mg, 3.9 mmol) in dry DMSO (2 mL) was added dropwise. The mixture was stirred at 120 C for 30 min, adjusted to pH 5-6 with aqueous NaHCO3 (5%) and extracted with ethyl acetate. The solvent was removed and the residue was purified by column chromatography using ethyl acetate: hexane (3:1) as eluent to afford 9 as a yellow solid (259.2 mg, 1.76 mmol, 65%). 1H NMR (400 MHz, DMSO-d6, delta = 2.49 ppm): 11.6 (s, 1H), 8.38 (dd, 1H, 3JH,H = 3.3 Hz, 4JH,H = 0.9 Hz), 7.87 (dd, 1H, 3JH,H = 5.0 Hz, 4JH,H = 1.1 Hz), 7.01 (dd, 1H, 3JH,H = 4.8 Hz, 4JH,H = 3.5 Hz). 13C-{1H} NMR (150 MHz, DMSO-d6, delta = 39.5 ppm): 183.0, 164.0, 160.0, 155.2, 132.6, 119.0, 112.9. C7H6N2O2. Found: C 56.66, H 2.83, N 18.72; requires: C 56.76, H 2.72, N 18.91.
31%		A suspension of <strong>[5654-97-7]7-azaoxindole</strong> (500 mg, 3.7 mmol) and N-bromosuccinimide (690.6 mg, 3.9 mmol) in dry DMSO (13 mL) was stirred at 60 C for 2 h and at 95 C for 8 h under reduced pressure (100 hPa). The mixture was adjusted to pH 5-6 with aqueous NaHCO3 (5%) and extracted with ethyl acetate. The solvent was removed and the residue was purified by column chromatography using ethyl acetate : hexane (3:1) as eluent to afford a yellow solid (170 mg, 1.15 mmol, 31 %). 1H-NMR (400 MHz, DMSO-d6, delta = 2.49 ppm): 11.6 (s, 1H, NH), 8.38 (dd, 1H, 3JH,H = 5.2 Hz, 4JH,H = 1.8 Hz, 6-CH), 7.87 (dd, 1H, 3JH,H = 7.5 Hz, 4JH,H = 0.9 Hz, 4-CH), 7.09 (dd, 1H, 3JH,H = 7.4 Hz, 4JH,H = 5.2 Hz, 5-CH).

References: [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 247 - 255.
[2]Patent: EP2199292,2010,A1 .Location in patent: Page/Page column 10.
[3]Helvetica Chimica Acta,1941,vol. 24,p. 141E,145E,150E.

23
[ 5654-97-7 ]
[ 126807-20-3 ]

References: [1]Helvetica Chimica Acta,1941,vol. 24,p. 141E,145E,150E.

24
[ 5654-97-7 ]
3-(3-oxo-3H-benzo[b]thiophen-2-ylidene)-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]

References: [1]Helvetica Chimica Acta,1941,vol. 24,p. 141E,145E,150E.

25
[ 5654-97-7 ]
3-amino-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]

References: [1]Helvetica Chimica Acta,1941,vol. 24,p. 141E,145E,150E.

26
[ 6443-85-2 ]
[ 5654-97-7 ]

References: [1]Journal of the American Chemical Society,1959,vol. 81,p. 740,742.

27
[ 6635-88-7 ]
[ 5654-97-7 ]

References: [1]Journal of the American Chemical Society,1959,vol. 81,p. 740,742.

28
[ 101012-32-2 ]
[ 5654-97-7 ]

References: [1]Journal of the American Chemical Society,1959,vol. 81,p. 740,742.

29
[ 6959-48-4 ]
[ 5654-97-7 ]

References: [1]Journal of the American Chemical Society,1959,vol. 81,p. 740,742.

30
[ 5654-97-7 ]
[ 36805-97-7 ]
[ 295327-35-4 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide;	Monomer 9: 3-Dimethylaminomethylene-<strong>[5654-97-7]7-azaoxindole</strong> This monomer was generated in situ (during library synthesis) from <strong>[5654-97-7]7-azaoxindole</strong> and dimethylformamide di-t-butylacetal in DMF.
	In DMF (N,N-dimethyl-formamide); at 20℃; for 1h;	This monomer was generated in situ (during library synthesis) from 7-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: US6369086,2002,B1 .
[2]Patent: US6350747,2002,B1 .Location in patent: Page column 74, 76.

31
methyl 2-(3-nitropyridin-2-yl)acetate [ No CAS ]
[ 5654-97-7 ]

References: [1]Patent: US6350747,2002,B1 .Location in patent: Page column 37-38.

32
[ 110-89-4 ]
[ 5654-97-7 ]
N-(2,4-dimethoxybenzyl)-N-(((5S)-3-(3-fluoro-4-formylphenyl)-2-oxo-1,3-oxazolidin-5-yl)methyl)acetamide [ No CAS ]
N-(2,4-dimethoxybenzyl)-N-(((5S)-3-(3-fluoro-4-((Z)-(2-oxo-1,2-dihydro-3H-pyrrolo(2,3-b)pyridin-3-ylidene)methyl)phenyl)-2-oxo-1,3-oxazolidin-5-yl)methyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; ethanol;	N-(2,4-dimethoxybenzyl)-N-(((5S)-3-(3-fluoro-4-((Z)-(2-oxo-1,2-dihydro-3H-pyrrolo(2,3-b)pyridin-3-ylidene)methyl)phenyl)-2-oxo-1,3-oxazolidin-5-yl)methyl)acetamide A suspension of Example 1C (200 mg) in ethanol (3 mL) was treated with <strong>[5654-97-7]1,3-dihydro-2H-pyrrolo(2,3-b)pyridin-2-one</strong> (81 mg), and piperidine (15 muL), sealed, heated to 100 C. for 24 hours, cooled to room temperature, and concentrated.. The concentrate was purified by flash column chromatography on silica gel with 2:98 methanol/dichloromethane to provide the desired product. MS (ESI(+)) m/e 548 (M+H)+; 1H NMR (300 MHz, DMSO-d6) delta 8.10 (t, 1H), 7.82 (t, 1H), 7.62 (m, 2H), 7.50 (d, 1H), 7.02-6.89 (m, 2H), 6.62-6.45 (m, 4H), 4.88 (m, 1H), 4.54-4.42 (m, 2H), 4.16 (t, 1H), 3.80 (m, 2H), 3.75 (s, 6H), 3.52 (m, 1H), 2.05 (s, 3H).

References: [1]Patent: US2002/91107,2002,A1 .

33
[ 113423-51-1 ]
[ 7440-66-6 ]
[ 5654-97-7 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium chloride; In tetrahydrofuran; CHCl3:MeOH;	b 7-Azaoxindole A solution of 3,3-dibromo-7-azaoxindole (2.0 g, 7.2 mmol) in THF (50 mL) is stirred at room temperature and a saturated aqueous solution of NH4Cl is added. Activated zinc powder is added and the reaction mixture is stirred for 2 hours. The zinc is removed by filtration through a pad of diatomaceous earth and the organic layer is separated. The aqueous layer is extracted with THF (10 mL) and the combined organic layers are dried over anhydrous MgSO4, filtered and evaporated. The residue is slurried in 10:1 CHCl3:MeOH (15 mL) and filtered through a pad of silica gel and the filtrate is evaporated. The residue is triturated with water and the solid is collected by filtration and dried under vacuum to give 7-azaoxindole, 0.668 g (70%). 1H NMR (DMSO-d6) delta10.94 (s, 1H), 8.02 (d, 1H, J=5.2 Hz), 7.52 (d, 1H, J=6.8 Hz), 6.90 (dd, 1H, J=6.8, 5.2 Hz), 3.53 (s, 2H). MS(AP-ve) 133 (100) (M-H)
	With ammonium chloride; In tetrahydrofuran; CHCl3:MeOH;	b 1,3-Dihydro-2H-pyrrolo[2,3-b]pyridin-2-one A solution of 3,3-dibromo-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (2.0 g, 7.2 mmol) in THF (50 mL) was stirred at room temperature, and a saturated aqueous solution of NH4Cl was added. Activated zinc powder was added, and the reaction mixture was stirred for 2 hours. The zinc was removed by filtration through a pad of diatomaceous earth, and the organic layer was separated. The aqueous layer was extracted with THF (10 mL), and the combined organic layers were dried over anhydrous MgSO4, filtered and evaporated. The residue was slurried in 10:1 CHCl3:MeOH (15 mL) and filtered through a pad of silica gel, and the filtrate was evaporated. The residue was triturated with water, and the solid was collected by filtration and dried under vacuum to give the title compound, 0.668 g (70%). 1H NMR (d6-DMSO) delta10.94 (s, 1H), 8.02 (d, 1H, J=5.2 Hz), 7.52 (d, 1H, J=6.8 Hz), 6.90 (dd, 1H, J=6.8, 5.2 Hz), 3.53 (s, 2H). MS (AP-ve) 133 (100) (M-H)
	With ammonium chloride; In tetrahydrofuran; CHCl3:MeOH;	b 1,3-Dihydro-2H-pyrrolo[2,3-b]pyridin-2-one A solution of 3,3-dibromo-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (2.0 g, 7.2 mmol) in THF (50 mL) was stirred at room temperature, and a saturated aqueous solution of NH4Cl was added. Activated zinc powder was added, and the reaction mixture was stirred for 2 h. The zinc was removed by filtration through a pad of diatomaceous earth, and the organic layer was separated. The aqueous layer was extracted with THF (10 mL), and the combined organic layers were dried over anhydrous MgSO4, filtered and evaporated. The residue was slurried in 10:1 CHCl3:MeOH (15 mL) and filtered through a pad of silica gel, and the filtrate was evaporated. The residue was triturated with water, and the solid was collected by filtration and dried under vacuum to give the title compound, 0.668 g (70%). 1H NMR (d6-DMSO) delta 10.94 (s, 1H), 8.02 (d, 1H, J=5.2 Hz), 7.52 (d, 1H, J=6.8 Hz), 6.90 (dd, 1H, J=6.8, 5.2 Hz), 3.53 (s, 2H). MS (AP-ve) 133 (100) (M-H).

References: [1]Patent: US6369086,2002,B1 .
[2]Patent: US6369086,2002,B1 .
[3]Patent: US6624171,2003,B1 .

34
[ 5654-97-7 ]
[ 63-74-1 ]
[ 36805-97-7 ]
[ 295327-24-1 ]

Yield	Reaction Conditions	Operation in experiment
36 mg (21%)	With methanesulfonic acid; sodium hydrogencarbonate; In methanol; ethanol; water; N,N-dimethyl-formamide;	Example 3A 4-[(2-Oxo-1,2-dihydro-3H-pyrrolo[2,3-b]pyridin-3-ylidene)methyl]amino}benzenesulfonamide Dimethylformamide di-tert-butyl acetal (180 mg, 0.89 mmol) was added to a solution of 1,2-dihydro-3H-pyrrolo[2,3-b]pyridin-2-one (70 mg, 0.52 mmol) in 0.25 ml DMF, and the reaction mixture was slowly warmed to 100 C. The cooled solution was then diluted with 5 ml of ethanol. Sulfanilamide (172 mg, 1.00 mmol) and methanesulfonic acid (60 mg, 0.63 mmol) were added, and the reaction mixture was stirred at reflux for 2 hours. The cooled solution was diluted with 4 ml of water, treated with NaHCO3 (70 mg, 0.83 mmol) and stirred 10 min. The resulting solid was filtered, washed with water and ethanol, and then suspended in boiling methanol and filtered upon cooling. Inorganics were removed by filtration through a short silica gel column, eluding with DMF. The resulting solution was diluted with an equal volume of ice water, and the suspension was refrigerated overnight. The solid was isolated by filtration and dried to give 36 mg (21%) of the title compound as a yellow solid: 1H NMR (400 MHz, DMSO-d6) (4:1 ratio of Z:E isomers): delta (Z) 11.07 (s, 1H), 10.76 (d, J=12.4 Hz, 1H), 8.67 (d, J=12.5 Hz, 1H), 7.92 (d, J=5.1 Hz, 1H), 7.84 (d, J=7.3 Hz,
36 mg (21%)	With methanesulfonic acid; sodium hydrogencarbonate; In methanol; ethanol; water; N,N-dimethyl-formamide;	EXAMPLE 3 4-[(2-oxo-1,2-Dihydro-3H-pyrrolo[2,3-b]pyridin-3-ylidene)methyl]amino}benzenesulfonamide Dimethylformamide di-tert-butyl acetal (180 mg, 0.89 mmol) was added to a solution of 1,2-dihydro-3H-pyrrolo[2,3-b]pyridin-2-one (70 mg, 0.52 mmol) in 0.25 ml DMF, and the reaction mixture was slowly warmed to 100 C. The cooled solution was then diluted with 5 ml of ethanol. Sulfanilamide (172 mg, 1.00 mmol) and methanesulfonic acid (60 mg, 0.63 mmol) were added, and the reaction mixture was stirred at reflux for 2 h. The cooled solution was diluted with 4 ml of water, treated with NaHCO3 (70 mg, 0.83 mmol) and stirred 10 min. The resulting solid was filtered, washed with water and ethanol, and then suspended in boiling methanol and filtered upon cooling. Inorganics were removed by filtration through a short silica gel column, eluding with DMF. The resulting solution was diluted with an equal volume of ice water, and the suspension was refrigerated overnight. The solid was isolated by filtration and dried to give 36 mg (21%) of the title compound as a yellow solid: 1H NMR (400 MHz, DMSO-d6) (4:1 ratio of Z:E isomers): delta (Z) 11.07 (s, 1H), 10.76 (d, J=12.4 Hz, 1H), 8.67 (d, J=12.5 Hz, 1H), 7.92 (d, J=5.1 Hz, 1H), 7.84 (d, J=7.3 Hz, 1H), 7.77 (d, J=8.7 Hz, 2H), 7.55 (d, J=8.6 Hz, 2H), 7.25 (s, 2H), 6.93 (dd, J=7.3, 5.1 Hz, 1H); (E) 10.79 (s, 1H), 9.70 (d, J=13.4 Hz, 1H), 8.23 (d, J=7.3 Hz, 1H). ESI-MS m/z 315 (M-H). Anal. Calcd. for C14H12N4O3S. 0.5 H2O: C, 51.68; H, 4.03; N, 17.03. Found: C, 51.75; H, 3.95; N, 17.26.

References: [1]Patent: US6369086,2002,B1 .
[2]Patent: US6624171,2003,B1 .

35
[ 5654-97-7 ]
[ 36805-97-7 ]
3-dimethylaminomethylene-1,3-dihydropyrrolo[2,3-b]pyridin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide;	3-[(Dimethylamino)methylidene]-1H-pyrrolo[2,3-b]pyridin-2-one This compound was prepared in situ (during library synthesis) from <strong>[5654-97-7]1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one</strong> and dimethylformamide di-t-butylacetal in DMF.

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

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
[ 5654-97-7 ]

Amides

A119767 [67046-22-4]

6,7-Dihydro-5H-pyrido[2,3-b]azepin-8(9H)-one

Similarity: 0.93

A134490 [1190314-60-3]

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

Similarity: 0.88

A205059 [183208-34-6]

5-Bromo-1H-pyrrolo[2,3-b]pyridin-2-one

Similarity: 0.87

A158079 [1190314-85-2]

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

Similarity: 0.86

A124267 [1086064-49-4]

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

Similarity: 0.84

Related Parent Nucleus of
[ 5654-97-7 ]

Other Aromatic Heterocycles

A119767 [67046-22-4]

6,7-Dihydro-5H-pyrido[2,3-b]azepin-8(9H)-one

Similarity: 0.93

A134490 [1190314-60-3]

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

Similarity: 0.88

A205059 [183208-34-6]

5-Bromo-1H-pyrrolo[2,3-b]pyridin-2-one

Similarity: 0.87

A158079 [1190314-85-2]

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

Similarity: 0.86

A124267 [1086064-49-4]

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

Similarity: 0.84

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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 5654-97-7

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