26956-43-4|Furo[3,2-c]pyridin-4(5H)-one| Ambeed

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Quality Control of [ 26956-43-4 ] Purity: 95% SDS Specification

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Product Details of [ 26956-43-4 ]

CAS No. :	26956-43-4
Formula :	C₇H₅NO₂
M.W :	135.12
SMILES Code :	O=C1C2=C(OC=C2)C=CN1
MDL No. :	MFCD00183939
InChI Key :	FYNCIYHECMWXPK-UHFFFAOYSA-N
Pubchem ID :	288746

Safety of [ 26956-43-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H320-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 26956-43-4 ]

* 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 [ 26956-43-4 ]

[ 26956-43-4 ] Synthesis Path-Downstream 1~35

1
[ 20689-54-7 ]
[ 26956-43-4 ]

References: [1]Journal of Heterocyclic Chemistry,1971,vol. 8,p. 57 - 60.
[2]Journal of Medicinal Chemistry,1989,vol. 32,p. 1147 - 1156.

2
[ 26956-43-4 ]
[ 54415-78-0 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1974,p. 1531 - 1536.

3
[ 26956-43-4 ]
[ 33007-12-4 ]

References: [1]Bulletin de la Societe Chimique de France,1971,p. 1727 - 1730.

4
[ 26956-43-4 ]
[ 33007-13-5 ]

References: [1]Bulletin de la Societe Chimique de France,1971,p. 1727 - 1730.

5
[ 26956-43-4 ]
[ 31270-80-1 ]

Yield	Reaction Conditions	Operation in experiment
81%		Reference Example 4 4-chlorofuro[3,2-c]pyridine; [Show Image] <strong>[26956-43-4]Furo[3,2-c]pyridin-4(5H)-one</strong> (72.2 g, 534 mmol) was added to phosphorus oxychloride (100 mL) heated to 120C, and the mixture was stirred for 30 min. The solvent was evaporated under reduced pressure. Ice-cooled water was added to the residue, and the mixture was basified with 8M aqueous sodium hydroxide solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70) to give the title compound (66.1 g, yield 81%). 1H-NMR (CDCl3) delta: 7.13 (1H, dd, J = 2.2, 1.0 Hz), 7.79 (1H, dd, J = 5.8, 1.0 Hz), 8.27 (1H, d, J = 2.2 Hz), 8.32 (1H, d, J = 5.8 Hz).
	With trichlorophosphate; at 120℃; for 3h;	5H-Furo [3,2-c] pyridin-4-one (5.9 g) was suspended with POCI3 (12 ml) and the reaction mixture was stirred for 3 hours at 120 C. After evaporating POCI3, crushed ice was added and poured into the mixture of ethyl acetate and saturated NaHCO3. The corresponding organic phase was separated and dried over NA2SO4 and then concentrated in vacuo. The resultant residue was purified by chromatography on a silica gel column to afford 4-chloro-furo [3,2-c] pyridine (5.6 g) 1 H NMR (400MHZ, DMSO-D6) ppm 8.31 (d, J = 5.8Hz, 1H), 8.26 (d, J = 2.3Hz, 1H), 7.79 (dd, J = 1.0, 5.6 Hz, 1H), 7.13 (dd, J=1.0, 2.3 Hz, 1 H).
	With trichlorophosphate; In acetonitrile; at 110℃; for 0.0833333h;Microwave irradiation;	General procedure: A solution of 6,7-dimethoxyisoquinolin-1(2H)-one(200 mg, 0.97 mmol), phosphoryl trichloride (0.268 mL, 2.92 mmol) inacetonitrile (5 mL) was stirred at 110 C for 5 minutes under microwaveirradiation. The reaction was quenched with a saturated aqueous sodium bicarbonatesolution and stirred at ambient temperature for 1 h. It was filtered throughcelite and washed with ethyl acetate. The filtrate was concentrated to dryness.The crude material was purified by flash chromatography, eluting with heptanesand ethyl acetate (1:0 to 0:1) to give the desired product as a gum (99 mg,45.4 %).

	With trichlorophosphate; for 3h;Heating / reflux;	[0155] Furopyridone (6,3. 26 g, 24.15 mmol) is treated with phosphorus oxychloride (10 ml) at refluxing temperature for 3 hours. After cooling, the dark solution is poured into ice and basified with aqueous sodium hydroxide to pH-9. The mixture is extracted with chloroform. After evaporation of the chloroform, the brown oil is applied to flash column chromatography on silica gel to give chlorofuropyridine as yellow crystalline solid (7).
	With trichlorophosphate; at 120 - 140℃; for 2.5h;	Next, Compound (3) (60.0 g, 444 mmol) and phosphorus oxychloride (POCl3) (62 mL, 666 mmol) were added into a reaction bottle. After heating the reaction bottle to 120-140 C. for 2.5 hours, the reaction bottle was cooled to 25 C. The reaction was quenched by water under ice bath. Next, the reaction mixture was neutralized with sodium hydroxide. The mixture was extracted with ethyl acetate (EA) and water. Next, an organic phase was separated and concentrated. Next, after removing water and concentrating, the result was purified by column chromatography. Compound (4) was obtained. The synthesis pathway of the above reaction was as follows:

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 250 - 254.
[2]Journal of Medicinal Chemistry,1989,vol. 32,p. 1147 - 1156.
[3]Patent: EP2100895,2009,A1 .Location in patent: Page/Page column 44-45.
[4]Bulletin de la Societe Chimique de France,1971,p. 1727 - 1730.
[5]Journal of Heterocyclic Chemistry,1971,vol. 8,p. 57 - 60.
[6]Patent: WO2004/100947,2004,A2 .Location in patent: Page 21; 16.
[7]Chemical and Pharmaceutical Bulletin,2009,vol. 57,p. 34 - 42.
[8]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3199 - 3203.
[9]Patent: WO2005/67900,2005,A2 .Location in patent: Page/Page column 39-40.
[10]Patent: US2020/24294,2020,A1 .Location in patent: Paragraph 0041; 0046.

6
[ 539-47-9 ]
[ 26956-43-4 ]

References: [1]Journal of Heterocyclic Chemistry,1971,vol. 8,p. 57 - 60.
[2]Journal of Medicinal Chemistry,1989,vol. 32,p. 1147 - 1156.
[3]Patent: WO2013/163244,2013,A1 .
[4]Patent: WO2016/37578,2016,A1 .
[5]Heterocycles,2017,vol. 95,p. 251 - 267.
[6]Patent: WO2005/67900,2005,A2 .

7
[ 33007-15-7 ]
[ 26956-43-4 ]

References: [1]Bulletin de la Societe Chimique de France,1971,p. 1727 - 1730.

8
[ 68-12-2 ]
[ 26956-43-4 ]
[ 86518-17-4 ]

References: [1]Tetrahedron,1983,vol. 39,p. 1777 - 1782.

9
[ 59898-36-1 ]
[ 26956-43-4 ]

Yield	Reaction Conditions	Operation in experiment
	With tributyl-amine; In diphenylether; at 230℃; for 0.5h;	Next, tri-n-butylamine ((nBu)3N) (41.3 ml, 500 mmol) and diphenyl ether (21.7 ml) were added into a reaction bottle. Next, after heating the reaction bottle to 230 C., Compound (2) (40.8 g, 250 mmol) (dissolved in 217 ml of diphenyl ether) was slowly added into the reaction bottle. After reacting for half hour, n-hexane was added into the reaction bottle. After filtrating and collecting the solid, Compound (3) was obtained. The synthesis pathway of the above reaction was as follows:

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 1147 - 1156.
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 250 - 254.
[3]Patent: US2020/24294,2020,A1 .Location in patent: Paragraph 0041; 0045.

10
[ 26956-43-4 ]
[ 76312-04-4 ]

References: [1]Archiv der Pharmazie,1981,vol. 314,p. 156 - 162.

11
[ 107-13-1 ]
[ 26956-43-4 ]
[ 74-88-4 ]
4-(1-cyanoethoxy)furo<3,2-c>pyridine [ No CAS ]
(1R^*,2aS^*,7bS^*)-1-cyano-4-oxo-1,2,2a,3,4,7b-hexahydrocyclobuta<g>furo<3,2-c>pyridine [ No CAS ]
(2S^*,2aR^*,7bR^*)-2-cyano-4-oxo-1,2,2a,3,4,7b-hexahydrocyclobuta<g>furo<3,2-c>pyridine [ No CAS ]
(2R^*,2aR^*,7bR^*)-2-cyano-3-methyl-4-oxo-1,2,2a,3,4,7b-hexahydrocyclobuta<g>furo<3,2-c>pyridine [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 1573 - 1580.

12
[ 107-13-1 ]
[ 26956-43-4 ]
4-(1-cyanoethoxy)furo<3,2-c>pyridine [ No CAS ]
(1S^*,2aS^*,7bS^*)-1-cyano-4-oxo-1,2,2a,3,4,7b-hexahydrocyclobuta<g>furo<3,2-c>pyridine [ No CAS ]
(1R^*,2aS^*,7bS^*)-1-cyano-4-oxo-1,2,2a,3,4,7b-hexahydrocyclobuta<g>furo<3,2-c>pyridine [ No CAS ]
(2S^*,2aR^*,7bR^*)-2-cyano-4-oxo-1,2,2a,3,4,7b-hexahydrocyclobuta<g>furo<3,2-c>pyridine [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 1573 - 1580.

13
[ 107-13-1 ]
[ 26956-43-4 ]
4-(1-cyanoethoxy)furo<3,2-c>pyridine [ No CAS ]
(1R^*,2aS^*,7bS^*)-1-cyano-4-oxo-1,2,2a,3,4,7b-hexahydrocyclobuta<g>furo<3,2-c>pyridine [ No CAS ]
(2S,2aR,7bS)-4-Oxo-1,2,2a,3,4,7b-hexahydro-7-oxa-3-aza-cyclobuta[e]indene-2-carbonitrile [ No CAS ]
(2S^*,2aR^*,7bR^*)-2-cyano-4-oxo-1,2,2a,3,4,7b-hexahydrocyclobuta<g>furo<3,2-c>pyridine [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 1573 - 1580.

14
[ 26956-43-4 ]
[ 74-88-4 ]
5-methylfuro<3,2-c>pyridin-4(5H)-one [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 1573 - 1580.

15
[ 57420-06-1 ]
[ 108-24-7 ]
[ 26956-43-4 ]
Acetic acid furo[3,2-c]pyridin-7-yl ester [ No CAS ]
Acetic acid furo[3,2-c]pyridin-6-yl ester [ No CAS ]
[4,5']Bi[furo[3,2-c]pyridinyl]-4'-one [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1996,vol. 33,p. 647 - 654.

Yield	Reaction Conditions	Operation in experiment
49 g (34%)		Example 1 Furo[3,2-c]pyridin-4(5H)-one, IV-2 (X=O) A solution of 21 (177 g, 1.1 mol) in CH2 Cl2 was added dropwise to mechanically stirred biphenyl (450 g, 2.5 mol) at an internally monitored temperature of approximately 230 C. (the biphenyl may be dissolved in CH2 Cl2 to facilitate handling and the CH2 Cl2 allowed to evaporate as the solution is being heated to 230 C.). The rate of addition is regulated to maintain an internal reaction temperature above 200 C. and to control the violent CH2 Cl2 evaporation as the azide solution is added. After the addition was complete, the reaction solution was allowed to cool to approximately 100 C. and maintained at that temperature while several extractions with boiling water were carried out. The decanted aqueous phases were cooled and the resulting precipitate filtered. Recrystallization from water yielded 49 g (34%) of solid.

18
[ 3601-89-6 ]
[ 26956-43-4 ]
C₂₈H₂₅NO₇ [ No CAS ]

References: [1]Journal of the American Chemical Society,2003,vol. 125,p. 9638 - 9646.

19
[ 26956-43-4 ]
[ 603301-02-6 ]

Yield	Reaction Conditions	Operation in experiment
16.10%	With N-Bromosuccinimide; In acetonitrile; at 0 - 20℃; for 1.33333h;	To a mixture of furo [3 2-c] pyridin-4 (5H) -one (5 g 37.0 mmol) in MeCN (50 mL) was added a solution of NBS (8.56 g 48.1 mmol) in MeCN at 0 over 10 min. The resulting suspension was stirred at 0 for 1 h and warmed to rt for 10 min. Water (250 mL) and saturated aqueous NaHCO3(10 mL) ware added to the mixture. Off-white solids ware collected by filtration and dried to afford 7-bromofuro [3 2-c] pyridin-4 (5H) -one (1.5 g 5.96 mmol 16.10 yield) 1HNMR(400 MHz CD3OD) delta 7.82 (d J 2.0 Hz 1H) 7.51 (s 1H) 7.05 (d J 2.4 Hz 1H) ES-LCMS m/z 214.0 215.9 (M+H)
	With N-Bromosuccinimide; In methanol; acetonitrile; at 0 - 20℃; for 18h;	Preparation 20; 7-Bromofuro [3,2-c] pyridine; 7-Bromo-5H-furoF3, 2-clpyn; Add N-bromosuccinimide (63.16 g, 354.9 mmol) as a solution in anhydrous acetonitrile (480 mL) to a suspension of 5H-furo [3,2-c] pyridin-4-one (36.9 g, 273 mmol) in anhydrous acetonitrile (740 mL) at 0 C over 1 hour. Warm to room temperature, add anhydrous methyl alcohol (1.5 L) and stir at room temperature for 18 hours. Quench with water (20 ml) and saturated sodium bicarbonate (20 mL), concentrate to a volume of 1.3 liters, and pour into water (1.3 L). Collection of the precipitate by filtration and drying (vacuum oven 2 days 40-60 C) gives the title compound as an off-white solid. ESMS: (m/z) = 213.9, 215.9 (M++1).

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 899 - 903.
[2]Patent: WO2016/37578,2016,A1 .Location in patent: Page/Page column 146; 147.
[3]Patent: WO2003/76442,2003,A1 .Location in patent: Page/Page column 38-39.

20
[ 29080-01-1 ]
[ 26956-43-4 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,2-dichloro-benzene; at 180℃; for 1h;Microwave irradiation; Inert atmosphere;	General procedure: A solution of acrylic acid 1 (0.30 mmol), DPPA (0.90 mmol), and Et3N (0.90 mmol) in 1,2-dichlorobenzene (3 mL) were stirred at 60 C for 15 min to generate in sute the isocyanate (monitored the disappearance of acrylic acid by TLC), and then was heated under microwave irradiation at 180 C for 1 h. After cooling to an ambient temperature, the reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, 10 g) using EtOAc-hexane (1:9 v/v) as an eluent to give the pyridone 5. Furo[3,2-c]pyridin-4-one 5a IR (ATR) nu: 1652 cm-1. mp 223-224 C (EtOAc-hexane). 1H-NMR (300 MHz, DMSO-d6) delta: 6.66 (1H, d, J = 7.3 Hz), 7.01 (1H, d, J = 2.1 Hz), 7.31 (1H, d, J = 7.3 Hz), 7.55 (1H, d, J = 2.1 Hz), 12.14 (1H, br s). 13C-NMR (75 MHz, DMSO-d6) delta: 94.7, 106.8, 119.9, 122.1, 128.9, 131.5, 144.0. MS (EI) m/z: 135 (M+); HRMS (EI) Calcd for C7H5NO2: 135.1220. Found: 135.1238.

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 250 - 254.
[2]Heterocycles,2017,vol. 95,p. 251 - 267.

21
[ 6974-32-9 ]
[ 26956-43-4 ]
[ 444898-86-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 562 - 565.

22
[ 29632-74-4 ]
[ 26956-43-4 ]
5-(4-amino-3-fluoro-phenyl)-5H-furo[3,2-c]pyridin-4-one [ No CAS ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 7677 - 7680.

23
[ 26956-43-4 ]
[ 444898-99-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 562 - 565.

24
[ 26956-43-4 ]
C₁₂H₁₆NO₁₅P₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 562 - 565.

25
[ 98-01-1 ]
linear tetraamine fac-Cr(CO)3 complex [ No CAS ]
[ 26956-43-4 ]