[ CAS No. 5832-44-0 ] {[proInfo.proName]}

Name: 5832-44-0|4-Methyl-3-nitropyridine|97%
Brand: Ambeed
SKU: A161180
Price: 13.0 USD
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Quality Control of [ 5832-44-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 5832-44-0 ]

CAS No. :	5832-44-0	MDL No. :	MFCD00051829
Formula :	C₆H₆N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JLNRJMGYBKMDGI-UHFFFAOYSA-N
M.W :	138.12	Pubchem ID :	521828
Synonyms :

Calculated chemistry of [ 5832-44-0 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	38.02
TPSA :	58.71 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.4 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.15
Log Po/w (XLOGP3) :	1.05
Log Po/w (WLOGP) :	1.3
Log Po/w (MLOGP) :	0.41
Log Po/w (SILICOS-IT) :	-0.35
Consensus Log Po/w :	0.71

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.74
Solubility :	2.54 mg/ml ; 0.0184 mol/l
Class :	Very soluble
Log S (Ali) :	-1.87
Solubility :	1.85 mg/ml ; 0.0134 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.76
Solubility :	2.38 mg/ml ; 0.0172 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.72

Safety of [ 5832-44-0 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P280-P310-P305+P351+P338	UN#:	2810
Hazard Statements:	H302-H311-H332-H315-H319-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 5832-44-0 ]

* 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 [ 5832-44-0 ]
Downstream synthetic route of [ 5832-44-0 ]

[ 5832-44-0 ] Synthesis Path-Upstream 1~16

1
[ 5832-44-0 ]
[ 3430-27-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen In ethyl acetate for 0.5 h;	4-Methyl-3-nitropyridine (3.642 g, 26.37 mmol; Lancaster) in ethyl acetate (36 mL) was treated with 10percent Pd/C (0.25 g) under a hydrogen atmosphere (60 psi) for 30 minutes. The catalyst was removed by filtration and the solution was concentrated to provide the title product as a white solid (2.92 g, 100percent). MS (DCI/NH3) m/z 109 (M+H)+.

Reference： [1] Patent: EP1428824, 2004, A1, . Location in patent: Page 42
[2] Tetrahedron Letters, 2010, vol. 51, # 5, p. 786 - 789
[3] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 1, p. 99 - 104
[4] Bulletin de la Societe Chimique de France, 1992, # 1, p. 79 - 84
[5] Chemische Berichte, 1927, vol. 60, p. 2108
[6] Chemische Berichte, 1927, vol. 60, p. 2108

2
[ 5832-44-0 ]
[ 7440-44-0 ]
[ 7440-05-3 ]
[ 3430-27-1 ]

Reference： [1] Patent: US2002/193596, 2002, A1,

3
[ 5832-44-0 ]
[ 54920-82-0 ]

Reference： [1] Journal of the American Chemical Society, 1955, vol. 77, p. 2438

4
[ 2530-26-9 ]
[ 105-39-5 ]
[ 18699-87-1 ]
[ 5832-44-0 ]

Reference： [1] Journal of Organic Chemistry, 2008, vol. 73, # 17, p. 6793 - 6799

5
[ 23056-39-5 ]
[ 5832-44-0 ]

Reference： [1] Journal of the American Chemical Society, 1954, vol. 76, p. 3167
[2] Journal of Organic Chemistry, 1957, vol. 22, p. 138
[3] Journal of the American Chemical Society, 1954, vol. 76, p. 596,598

6
[ 108-89-4 ]
[ 5832-44-0 ]

Yield	Reaction Conditions	Operation in experiment
50 g	at -30℃; for 0.1 h;	60 g of the dinitrogen pentoxide solid collected in the step 1) of Example 1 was introduced, and 300 g of sulfur dioxide liquid was introduced at -30 ° C, and the mixture was sufficiently stirred and dissolved to be used. 30g of 4-methylpyridine at -30 under the sulfur dioxide into the liquid 120g, fully dissolved, slowly dropping sulfur dioxide pentoxide solution, the full reaction for 5min, the reaction solution was slowly added to 300g of ice water , Fully hydrolyzed and then adjusted to pH 8-9 by adding sodium carbonate. Add 290g toluene extraction twice combined extract, extract the solvent removed after vacuum distillation 3-nitro-4-methyl pyridine 39g, by gas chromatography detection, purity 99.0percent.

Reference： [1] Organic and Biomolecular Chemistry, 2005, vol. 3, # 3, p. 538 - 541
[2] Acta Chemica Scandinavica, 1994, vol. 48, # 12, p. 1001 - 1006
[3] Acta Chemica Scandinavica, 1994, vol. 48, # 2, p. 181 - 182
[4] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1995, # 6, p. 1211 - 1216
[5] Acta Chemica Scandinavica, 1996, vol. 50, # 6, p. 556 - 557
[6] Synthesis, 1997, # 3, p. 281 - 283
[7] Acta Chemica Scandinavica, 1999, vol. 53, # 2, p. 141 - 144
[8] Patent: CN106187870, 2016, A, . Location in patent: Page/Page column 0017; 0018; 0034; 0035

7
[ 21901-18-8 ]
[ 5832-44-0 ]

Reference： [1] Journal of the American Chemical Society, 1954, vol. 76, p. 3167

8
[ 2530-26-9 ]
[ 105-39-5 ]
[ 18699-87-1 ]
[ 5832-44-0 ]

Reference： [1] Journal of Organic Chemistry, 2008, vol. 73, # 17, p. 6793 - 6799

9
[ 15014-25-2 ]
[ 13091-23-1 ]
[ 5832-44-0 ]
[ 5435-54-1 ]

Reference： [1] Synthetic Communications, 1981, vol. 11, # 9, p. 743 - 750

10
[ 7647-01-0 ]
[ 54415-82-6 ]
[ 5832-44-0 ]

Reference： [1] Chemische Berichte, 1927, vol. 60, p. 2108

11
[ 5832-44-0 ]
[ 153813-70-8 ]

Reference： [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 7, p. 1106 - 1118
[2] Journal of the American Chemical Society, 1955, vol. 77, p. 2438
[3] Tetrahedron Letters, 1994, vol. 35, # 2, p. 219 - 222
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 21, p. 6495 - 6499
[5] Patent: WO2005/123685, 2005, A1,

12
[ 5832-44-0 ]
[ 21901-40-6 ]

Reference： [1] Journal of the Chemical Society. Perkin Transactions 1, 2001, # 4, p. 376 - 378

13
[ 5832-44-0 ]
[ 59290-82-3 ]

Reference： [1] Journal of the American Chemical Society, 1954, vol. 76, p. 3167

14
[ 15014-25-2 ]
[ 13091-23-1 ]
[ 5832-44-0 ]
[ 5435-54-1 ]

Reference： [1] Synthetic Communications, 1981, vol. 11, # 9, p. 743 - 750

15
[ 5832-44-0 ]
[ 24334-19-8 ]

Reference： [1] Molecules, 2014, vol. 19, # 9, p. 13342 - 13357
[2] Patent: WO2004/104001, 2004, A2,

16
[ 5832-44-0 ]
[ 133627-45-9 ]

Reference： [1] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 1, p. 99 - 104

[ 5832-44-0 ] Synthesis Path-Downstream 1~88

1
[ 23056-39-5 ]
[ 5832-44-0 ]

Reference： [1]Journal of the American Chemical Society,1954,vol. 76,p. 3167
[2]Journal of Organic Chemistry,1957,vol. 22,p. 138

2
[ 108-89-4 ]
[ 5832-44-0 ]

Yield	Reaction Conditions	Operation in experiment
50 g	With sulfur dioxide; dinitrogen pentoxide; at -30℃; for 0.1h;	60 g of the dinitrogen pentoxide solid collected in the step 1) of Example 1 was introduced, and 300 g of sulfur dioxide liquid was introduced at -30 C, and the mixture was sufficiently stirred and dissolved to be used. 30g of 4-methylpyridine at -30 under the sulfur dioxide into the liquid 120g, fully dissolved, slowly dropping sulfur dioxide pentoxide solution, the full reaction for 5min, the reaction solution was slowly added to 300g of ice water , Fully hydrolyzed and then adjusted to pH 8-9 by adding sodium carbonate. Add 290g toluene extraction twice combined extract, extract the solvent removed after vacuum distillation 3-nitro-4-methyl pyridine 39g, by gas chromatography detection, purity 99.0%.

Reference： [1]Organic and Biomolecular Chemistry,2005,vol. 3,p. 538 - 541
[2]Acta Chemica Scandinavica,1994,vol. 48,p. 1001 - 1006
[3]Acta Chemica Scandinavica,1994,vol. 48,p. 181 - 182
[4]Journal of the Chemical Society. Perkin transactions II,1995,p. 1211 - 1216
[5]Acta Chemica Scandinavica,1996,vol. 50,p. 556 - 557
[6]Synthesis,1997,p. 281 - 283
[7]Acta Chemica Scandinavica,1999,vol. 53,p. 141 - 144
[8]Patent: CN106187870,2016,A .Location in patent: Page/Page column 0017; 0018; 0034; 0035

3
[ 5832-44-0 ]
[ 4637-24-5 ]
[ 908847-23-4 ]

Yield	Reaction Conditions	Operation in experiment
45%	In N,N-dimethyl-formamide; at 120℃; for 13h;	Synthesis of (E)-N,N-dimethyl-2-(3-nitropyridine-4-yl)ethanamine[00301] To a solution of <strong>[5832-44-0]4-methyl-3-nitropyridine</strong> (1.0 equiv.) in DMF(5.5 M) was added l ,l-dimethoxy-N,N-dimethylmethaneamine (1.0 equiv.) and the solution was allowed to stir at 120 C for 13hrs. The reaction was cooled to room temperature, poured onto crushed ice and stirred for 5 min. The red solid was filtered and washed with cold water. The solid was recrystallized form hot MeOH to yield (E)-N,N- dimethyl-2-(3-nitropyridine-4-yl)ethanamine as the desired product in 45% yield.LC/MS (m/z): 194.0 (MH+), R, = 0.39 min.
	In DMF (N,N-dimethyl-formamide); at 140℃; for 2h;	Intermediate 12: (3R/S)-3-AMINO-L-FF (4R)-2, 2-DIMETHVL-1, 3-DIOXOLAN-4-VLLMETHVL -3, 4- dihvdro-1, 7-NAPHTHVRIDIN-2 (1H)-one 4-Methyl-nitropyridine (1.43 g, 10. 36MMOL) was dissolved in dry DMF (5ML) and dimethylformamide dimethyl acetal (2.0 g, 16.8 mmol) was added. The mixture was heated under nitrogen at 140C for 2 hours and then evaporated under reduced pressure to give (E)- N, N-DIMETHYL-2- (3-NITROPYRIDIN-4-YL) ethyleneamine as a dark red solid. This was added in one portion at ambient temperature to a stirred solution of sodium periodate (6.61 g, 31 mmol) in THF/Water 1: 1 (100 mL). After stirring for 2hr at ambient temperature the reaction mixture was filtered and the solid washed with ethyl acetate (100 mL). The washings were combined with the filtrate and organic layer separated. The aqueous was extracted with ethyl acetate x 100 mL) and the combined organic layers were washed with saturated aqueous sodium bicarbonate (100 mL) and brine (100 mL), dried (MGS04) and evaporated under reduced pressure to give a brown solid which was purified by column chromatography (DCM) to give 3-nitroisonicotinaldehyde (960mg, 61%). H NMR 8 : 7.8 (d, 1H); 9.15 (d, 1H); 9.4 (s, 1H) ; 10.4 (s, 1H) Methyl [(TERT-BUTOXYCARBONYL) AMINO] (dimethoxyphosphoryl) acetate (1.73g, 5.82 mmol) was dissolved in dry THF (20 mL) and cooled to-78 C under nitrogen. Tetramethylguanidine (638 mg, 5.55 mmol) was added and the solution stirred at-78 C for a further 10 mins. A solution of 3-nitroisonicotinaldehyde (804 mg, 5.29 mmol) in dry THF (5ML) was added dropwise. The resulting deep red solution was stirred for 2hrs AT-78C, then poured into a mixture of ethyl acetate (100 mL) and water (50 mL). The organic layer was separated, washed with water (2 x 50 mL) and brine (25 mL), dried (MGS04) and evaporated under reduced pressure to give a yellow oil, which was purified by column chromatography (EtOAc: isohexane 1: 1) to give METHYL-2- [ (TERT-BUTOXYCARBONYL) AMINO]-3- (3-NITROPYRIDIN-4- yl) acrylate as a 10: 1 mixture of Z/E isomers (1.57g, 92%). H NMR 8 : 1.3 (s, 9H); 1.4 (s, 0.9H) ; 3.55 (s, 0.3H) ; 3.8 (s, 3H); 6.6 (s, 0. 1H) ; 7.2 (s, 1H) ; 7.25 (d, 0. 1H) ; 7.5 (d, 1H) ; 8.75 (d, 0. 1H) ; 8.8 (s, 1. 1H) ; 8.85 (d, 1H) ; 9.2 (s, 0. 1H) ; 9.25 (s, 1H); MS m/z 322. Methyl 2-[(TERT-BUTOXYCARBONYL) AMINO]-3-(3NITROPYRIDIN-4-YL) ACRYLATE (10: 1 mixture of Z/E isomers) (1.57 g, 4.83 mmol) was dissolved in ethanol and 10% palladium on carbon catalyst (250 mg) was added. The mixture was stirred under 1 atmosphere of hydrogen at ambient temperature for 6 hours. After removing the catalyst by filtration through Celite, the filtrate was concentrated under reduced pressure to give a yellow oil which was purified by column chromatography (Eluent DCM/MEOH gradient 0-10%) to give tert-butyl (2-oxo- 1, 2,3, 4-TETRAHYDRO-1, 7-naphthyridine-3-yl) carbamate (284mg, 22%). H NMR 8 : 1.4 (s, 9H); 3.0 (m, 2H); 4.2 (m, 1H); 7.0 (d, 1H) ; 7.2 (d, LH) ; 8.1 (m, 2H); 10.36 (s, 1H); MS m/z 264. tert-Butyl (2-oxo-1, 2,3, 4-TETRAHYDRO-1, 7-naphthyridine-3-yl) carbamate (284mg) was dissolved in DCM (10 mL) and treated with trifluoroacetic acid (5 mL). After stirring at ambient temperature for 1 hour the reaction mixture was evaporated under reduced pressure and the residue triturated with ether (20 mL) to give a light brown solid which was collected by filtration, washed with ether and dried to give 3-amino-3, 4-DIHYDRO-1, 7-naphthyridin-2 (1H)- one (346 mg, 82%) as a bis trifluroacetate salt. H NMR 8 : 3.2 (m, 2H); 4.3 (m, 1H), 7.4 (d, 1H) ; 8.2 (s, 1H) ; 8.25 (d, 1H) ; 8.6 (b, 3H); 11.0 (s, 1H) Sodium hydride (1.18 g, 60% dispersion in oil, 29.4 mmol) was added to a suspension of (3R/S)-3-Amino-3, 4-DIHYDRO-1, 7-naphthyridin-2 (lH)-one (2.24 g, 9.4 mmol) in dry DMF (40 mL) and the mixture heated to 80 C and stirred for 30 mins. [ (4S)-2, 2-Dimethyl-1, 3- dioxolan-4-yl] methyl methanesulfonate (2 mL, 10.4 mmol) was added and the reaction stirred at 80 C for 19 h. The mixure was cooled, diluted with DCM (450 mL), purified using flash column chromatography (SI02, eluent: DCM to DCM: MeOH, 85: 15 to DCM: MeOH: NH40H, 80: 20: 0.7) and the volatiles removed under reduced pressure to afford the title compound (1. 1 g, 42%) as an oil. LH NMR O : 1.23 (m, 3H), 1.26 (s, 1. 8H), 1. 28 (s, 1.2H), 3.52 (m, 1H), 3.68 (m, 1H), 4.02 (m, 2H), 4.15 (m, 1H), 4.31 (m, 1H), 7.27 (br d, 1H), 8. 21 (d, 1H), 8. 55 (d, 1H) ; MS M/Z 278.

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 219 - 222
[2]Patent: WO2012/4217,2012,A1 .Location in patent: Page/Page column 148
[3]Tetrahedron Letters,2006,vol. 47,p. 5653 - 5656
[4]Patent: WO2005/20987,2005,A1 .Location in patent: Page/Page column 58

4
[ 5832-44-0 ]
[ 613-45-6 ]
[ 131073-19-3 ]

Reference： [1]European Journal of Medicinal Chemistry,1990,vol. 25,p. 467 - 477

5
[ 15014-25-2 ]
[ 13091-23-1 ]
[ 5832-44-0 ]
[ 5435-54-1 ]

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

6
[ 5832-44-0 ]
[ 67-66-3 ]
2-(dichloromethyl)-4-methyl-3-nitropyridine [ No CAS ]
2-(dichloromethyl)-4-methyl-5-nitropyridine [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 2671 - 2676

7
[ 5832-44-0 ]
[ 535-13-7 ]
2-(1-ethoxycarboethyl)-4-methyl-5-nitropyridine [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 2671 - 2676

8
[ 5832-44-0 ]
3-benzyl-6-azaindole [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 5653 - 5656

9
[ 5832-44-0 ]
3-N,N-diethylaminoethyl-6-azaindole [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 5653 - 5656

10
[ 5832-44-0 ]
3-cinnamyl-6-azaindole [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 5653 - 5656

11
[ 5832-44-0 ]
Dimethyl-[(E)-2-(3-nitro-pyridin-4-yl)-3-phenyl-propenyl]-amine [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 5653 - 5656

12
[ 5832-44-0 ]
3-(4-phenyl)benzyl-6-azaindole [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 5653 - 5656

13
[ 5832-44-0 ]
2-(phenyl-(6-azaindol-3-yl)methylene)malononitrile [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 5653 - 5656

14
[ 5832-44-0 ]
3-benzoyl-6-azaindole [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 5653 - 5656

15
[ 5832-44-0 ]
2-(3-furyl)-1H-pyrrolo[2,3-c]pyridine [ No CAS ]

Reference： [1]Synthesis,2003,p. 1671 - 1678

16
[ 5832-44-0 ]
[ 627511-03-9 ]

Reference： [1]Synthesis,2003,p. 1671 - 1678

17
[ 5832-44-0 ]
[ 627510-97-8 ]

Reference： [1]Synthesis,2003,p. 1671 - 1678

18
[ 5832-44-0 ]
2-(4-bromophenyl)-1H-pyrrolo[2,3-c]pyridine [ No CAS ]

Reference： [1]Synthesis,2003,p. 1671 - 1678

19
[ 5832-44-0 ]
[ 627511-00-6 ]

Reference： [1]Synthesis,2003,p. 1671 - 1678

20
[ 5832-44-0 ]
[ 627510-94-5 ]

Reference： [1]Synthesis,2003,p. 1671 - 1678

21
[ 5832-44-0 ]
2-(4-trifluoromethylphenyl)-1H-pyrrolo[2,3-c]pyridine [ No CAS ]

Reference： [1]Synthesis,2003,p. 1671 - 1678

22
[ 5832-44-0 ]
[ 627510-93-4 ]

Reference： [1]Synthesis,2003,p. 1671 - 1678

23
[ 5832-44-0 ]
[ 627510-99-0 ]

Reference： [1]Synthesis,2003,p. 1671 - 1678

24
[ 5832-44-0 ]
[ 120236-87-5 ]

Reference： [1]European Journal of Medicinal Chemistry,1990,vol. 25,p. 467 - 477

25
[ 5832-44-0 ]
[ 52090-68-3 ]

Reference： [1]Chemische Berichte,1927,vol. 60,p. 2108

26
[ 5832-44-0 ]
N-(4-methyl-[3]pyridyl)-benzamide; benzoate [ No CAS ]

Reference： [1]Chemische Berichte,1927,vol. 60,p. 2108

27
[ 21901-18-8 ]
[ 5832-44-0 ]

Reference： [1]Journal of the American Chemical Society,1954,vol. 76,p. 3167

28
[ 5832-44-0 ]
[ 54920-82-0 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 2438

29
[ 5832-44-0 ]
[ 109017-19-8 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 2438

30
[ 5832-44-0 ]
N-(3-nitro-[4]pyridylmethylene)-p-toluidine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 2438

31
[ 5832-44-0 ]
3t-(3-amino-[4]pyridyl)-acrylic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 2438

32
[ 5832-44-0 ]
3t-(3-nitro-[4]pyridyl)-acrylic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 2438

33
[ 5832-44-0 ]
2-thiazol-5-yl-1H-pyrrolo[2,3-c]pyridine [ No CAS ]

Reference： [1]Journal of medicinal chemistry,1972,vol. 15,p. 1168 - 1171

34
[ 5832-44-0 ]
[ 40068-82-4 ]

Reference： [1]Journal of medicinal chemistry,1972,vol. 15,p. 1168 - 1171

35
[ 5832-44-0 ]
[ 24334-18-7 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of potassium ethoxide (3. 1G, 36. 2MMOL) in diethyl ether (70mL) and ethanol (lOmL) under an argon atmosphere was added diethyl oxalate (4.9mL, 36. 2MMOL) and the reaction stirred at rt for 30min. A solution of 4-methyl-3- nitropyridine (5. 0g, 36. 2MMOL) in diethyl ether (20mL) was added resulting in the immediate FORMATION of a dark red precipitate. The reaction mixture was stirred at rt for 72h, then cooled to 0C and filtered. The solid was dissolved in water (500ML) acidified to pH 4 with acetic acid and the precipitate collected and dried to give the title compound as a red solid. 5N (d6 DMSO): 1.27 (3H, t), 4.25 (2H, q), 6.74 (1H, s), 8.34 (1H, d), 8.43 (1H, d), 8.98 (1H, s); m/z (ES+) = 239 [M+ H] +.

Reference： [1]Patent: WO2004/104001,2004,A2 .Location in patent: Page 33

36
[ 5832-44-0 ]
[ 31680-08-7 ]
C₁₄H₁₁N₃O₅ [ No CAS ]

Reference： [1]Patent: US2004/14759,2004,A1 .Location in patent: Page/Page column 12

37
[ 5832-44-0 ]
[ 4637-24-5 ]
(E)-N,N-dimethyl-2-(3-nitropyridin-4-yl)ethyleneamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In DMF (N,N-dimethyl-formamide); at 140℃; for 2h;	Intermediate 12: 3-Nitroisonicotinaldehyde; <strong>[5832-44-0]4-Methyl-3-nitropyridine</strong> (1.43 g, 10.36 mmol) was dissolved in dry DMF (5 ml) and dimethylformamide dimethyl acetal (2.0 g, 16.8 mmol) was added. The mixture was heated under nitrogen at 140C for 2 hours and then evaporated under reduced pressure to give (E)- N,N dimethyl-2-(3-nitropyridin-4-yl)ethyleneamine as a dark red solid. This was added in one portion at ambient temperature to a stirred solution of sodium periodate (6.61g, 31mmol) in THF/ Water 1:1 (100 ml). After stirring for 2hr at ambient temperature the reaction mixture was filtered and the solid washed with ethyl acetate (100 ml). The washings were combined with the filtrate and organic layer separated. The aqueous was extracted with ethyl acetate (2 x 100 ml) and the combined organic layers were washed with saturated aqueous sodium bicarbonate (100 ml) and brine (100 ml), dried (MgS04) and evaporated under reduced pressure to give a brown solid which was purified by column chromatography (DCM) to give 3-nitroisonicotinaldehyde (960 mg, 61 %). ¹H NMR: 7.8 (d, 1 H); 9.15 (d, 1 H); 9.4 (s, 1 H); 10.4 (s, 1H)

Reference： [1]Patent: WO2005/123685,2005,A1 .Location in patent: Page/Page column 65

38
[ 553-90-2 ]
[ 5832-44-0 ]
[ 865-33-8 ]
[ 501892-48-4 ]

Yield	Reaction Conditions	Operation in experiment
8.15 g (86%)	In diethyl ether;	EXAMPLE 10 N-[(1S,2R,4R)-7-azabicyclo[2.2.1]hept-2-yl]-1H-pyrrolo[2,3-c]pyridine-2-carboxamide dihydrochloride Potassium methoxide (2.8 g, 39.8 mmol) is combined with methyl oxalate (4.7 g, 39.8 mmol) in 80 ml Et2O in a dry flask under nitrogen. The suspension is diluted with 12 ml CH3OH, is treated dropwise with <strong>[5832-44-0]4-methyl-3-nitropyridine</strong> (5 g, 36.2 mmol) in 25 ml Et2O, and the black suspension is stirred 24 h at RT. The black solid is collected, washed with fresh Et2O, and is dried to give 8.15 g (86%) of potassium-3-methoxy-1-(3-nitropyridin-4-yl)-3-oxoprop-1-en-2-olate. HRMS (FAB) calcd for C9H8N2O5+H: 225.0511, found 225.0515 (M+H)+.

Reference： [1]Patent: US2003/105089,2003,A1

39
[ 5832-44-0 ]
[ 7440-44-0 ]
[ 7440-05-3 ]
[ 3430-27-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; In methanol;	EXAMPLE 280A 4-methyl-3-aminopyridine A mixture of <strong>[5832-44-0]4-methyl-3-nitropyridine</strong> (414.4 mg, 3 mmol) and palladium (10%) on carbon (100 mg) in methanol (5 mL) was flushed with hydrogen, and stirred under a hydrogen balloon for 5 hours. The mixture was then filtered through Celite, rinsed with methanol, and concentrated in vacuo. The residue was used without further purification.

Reference： [1]Patent: US2002/193596,2002,A1

40
[ 5832-44-0 ]
3-nitro-nicotinic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; potassium permanganate; In water;	Example 290A 3-nitro-nicotinic acid <strong>[5832-44-0]3-Nitro-4-methylpyridine</strong> (2 g, 14 mmol) in water (200 mL) was refluxed while a saturated solution of potassium permanganate (4.43 g, 28 mmol) in water (20 mL) was added dropwise over a 4 hour period. At the end of addition, the solution was refluxed for another two hours. The solution was filtered while hot, the brown manganese dioxide filter cake was extracted twice with hot water, and the filtrates were combined and concentrated in vacuo. Then the solid was redissolved with a minimum amount of water, and concentrated hydrochloric acid was added to acidify the solution to pH=3. The acidic solution was concentrated in vacuo to give 800 mg of brown product (carboxylic acid salt and KCl salt). The product mixture was carried for next step without further purification. Reference: Kataoka, M.; Morisawa, Y.; Kitano, N. J. Med. Chem. 1976, 30(4), 483-487.

Reference： [1]Patent: US2001/44445,2001,A1

41
[ 5832-44-0 ]
[ 378784-00-0 ]
3-amino-4-methylpiperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; ammonia;	3-Amino-4-methylpiperidine A quantity of 5.0 g of <strong>[5832-44-0]3-nitro-4-methylpyridine</strong>, 0.5 g of ruthenium oxide, 0.5 g of rhodium on aluminia, and 0.5 g of platinum oxide are suspended in 20 ml of ammonia solution and 10 ml of methanol. The mixture is subjected to high temperature and high pressure hydrogen gas. The desired product is obtained by an aqueous work up.

Reference： [1]Patent: US6329391,2001,B1

42
[ 5832-44-0 ]
[ 50-00-0 ]
[ 918153-30-7 ]

Yield	Reaction Conditions	Operation in experiment
10%	With N-benzyl-trimethylammonium hydroxide; In dimethyl sulfoxide; at 90℃; for 4h;	Example 6; Scheme F; A mixture of f-1 (0.0094 mol) and paraformaldehyde (0.0075 mol) in DMSO (4.5 ml) and triton B (0.35 ml) was stirred at 90C for 4 hours, and then purified by column chromatography over silica gel (eluent: CH2Cl2; 15mum). The pure fractions were collected and the solvent was evaporated, yielding: 0.15 g of intermediate f-2 (10%).

Reference： [1]Patent: WO2006/136562,2006,A1 .Location in patent: Page/Page column 26
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 1727 - 1746

43
[ 5832-44-0 ]
[ 95-92-1 ]
[ 24334-18-7 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 20℃; for 1h;	EXAMPLE 1Compound 1N-(1-methyl-1H-indol-5-yl)-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-c]pyridine-2-carboxamide1.1 ethyl 3-(3-nitropyridin-4-yl)-2-oxopropionate; 3.1 g (22.44 mmol) of <strong>[5832-44-0]4-methyl-3-nitropyridine</strong> and 16.39 g (112.22 mmol) of ethyl oxalate are placed in a 100 ml three-necked flask equipped with a magnetic stirrer and maintained under a flush of nitrogen. 3.69 ml (24.69 mmol) of 1,8-diaza-bicyclo[5.4.0]undec-7-ene are then added to the reaction medium stirred at room temperature. The reaction mixture is then stirred at room temperature for 1 hour and then diluted with a mixture of ethyl acetate (150 ml), water (100 ml) and acetic acid (4 ml). The mixture is extracted twice with ethyl acetate. The combined organic phases are washed with 100 ml of water, with 100 ml of saturated aqueous sodium chloride solution, dried over sodium sulfate and then concentrated under reduced pressure. The crude reaction product is then triturated from pentane, filtered and then heated in petroleum ether, filtered and dried under reduced pressure. 3.9 g (16.37 mmol) of product are thus isolated, and are used without further purification in the following step.1H NMR (CDCl3), delta (ppm): 9.4 (s, 1H); 8.9 (d, 1H); 7.4 (d, 1H) 4.65 (s, 2H); 4.5 (q, 2H); 1.4 (t, 3H).
		Ethyl 3-(3-nitro-4-pyridyl)-2-oxopropionate To a solution of 930 mg of sodium in 50 mL of absolute ethanol are rapidly added 26 mL of diethyl oxalate. The reaction medium is stirred for 15 minutes at 20 C. A solution of 3.8 g of <strong>[5832-44-0]4-methyl-3-nitropyridine</strong> in 50 mL of absolute ethanol is then added dropwise over 1 hour. The reaction medium is stirred for 4 hours at a temperature in the region of 20 C. and then concentrated under reduced pressure. The residue is taken up in 100 mL of ethyl ether and then filtered. The solid is stirred with 40 mL of 5N hydrochloric acid and then filtered, washed with water and dried under vacuum at 40 C. to give 6.2 g of ethyl 3-(3-nitro-4-pyridyl)-2-oxopropionate having the following characteristics: Mass spectrum (EI) m/z=238 [M+].

Reference： [1]Molecules,2014,vol. 19,p. 13342 - 13357
[2]Patent: US2008/125459,2008,A1 .Location in patent: Page/Page column 8
[3]Patent: US2008/139606,2008,A1 .Location in patent: Page/Page column 4-5; 8

44
[ 2530-26-9 ]
[ 105-39-5 ]
[ 18699-87-1 ]
[ 5832-44-0 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 6793 - 6799

45
[ 5832-44-0 ]
[ 1337991-80-6 ]
[ 1337991-79-3 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 16243 - 16250

46
[ 5832-44-0 ]
[ 1344141-44-1 ]

Reference： [1]Bioorganic and medicinal chemistry letters,2011,vol. 21,p. 6495 - 6499

47
[ 5832-44-0 ]
[ 1344141-46-3 ]

Reference： [1]Bioorganic and medicinal chemistry letters,2011,vol. 21,p. 6495 - 6499

48
[ 5832-44-0 ]
[ 4637-24-5 ]
[ 64679-69-2 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; for 2h;Reflux;	To a stirred solution of 3-nitro-4-methyl pyridine (4.14 g, 30 mmol) in DMF (10 mL) was added N,N-dimethylformamide dimethyl acetal (5.36 g, 45 mmol). The reaction mixture was refluxed for 2 h. Formation of alkene intermediate compound was observed on TLC and confirmed by the GCMS peak at for 193. the mixture was than cooled and was added sodium periodate (20 g, 90 mmol) in 150 mL THF:H2O (1:1) mixture. The reaction mixture was stirred at room temperature for 5-6 h followed by filtration and the filtrate was than rotary evaporated and extracted with ethyl acetate (3 X 50 mL). The organic layer was washed with brine, dried over sodium sulfate and concentrated to yield thick oil which was subjected to flash column chromatography (n-hexane:EtOAc, 60:40) to get the desired product as a brown solid (3.19 g, 70%).

Reference： [1]Bioorganic and medicinal chemistry letters,2011,vol. 21,p. 6495 - 6499

49
[ 14371-10-9 ]
[ 5832-44-0 ]
(S)-4-(3-nitro-pyridin-4-yl)-3-phenyl-butyraldehyde [ No CAS ]