Home Cart 0 Sign in  
X

[ CAS No. 23443-25-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 23443-25-6
Chemical Structure| 23443-25-6
Chemical Structure| 23443-25-6
Structure of 23443-25-6 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 23443-25-6 ]

Related Doc. of [ 23443-25-6 ]

Alternatived Products of [ 23443-25-6 ]

Product Details of [ 23443-25-6 ]

CAS No. :23443-25-6 MDL No. :MFCD15142684
Formula : C9H8N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :SSMACLPPRSQXHH-UHFFFAOYSA-N
M.W : 176.17 Pubchem ID :11378807
Synonyms :

Safety of [ 23443-25-6 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338 UN#:
Hazard Statements:H302 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 23443-25-6 ]

* 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.

  • Upstream synthesis route of [ 23443-25-6 ]
  • Downstream synthetic route of [ 23443-25-6 ]

[ 23443-25-6 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 23443-25-6 ]
  • [ 10261-82-2 ]
Reference: [1] Patent: WO2010/81874, 2010, A1,
  • 2
  • [ 23443-25-6 ]
  • [ 249889-68-7 ]
Reference: [1] Patent: EP1724268, 2006, A1, . Location in patent: Page/Page column 79
[2] Patent: US2014/336182, 2014, A1, . Location in patent: Paragraph 0323
[3] Patent: WO2008/124083, 2008, A2, . Location in patent: Page/Page column 50
[4] Patent: WO2007/113548, 2007, A1, . Location in patent: Page/Page column 153-154
  • 3
  • [ 23443-25-6 ]
  • [ 249889-68-7 ]
Reference: [1] Patent: EP1214314, 2005, B1, . Location in patent: Page/Page column 15
  • 4
  • [ 23443-25-6 ]
  • [ 881658-92-0 ]
YieldReaction ConditionsOperation in experiment
90% With phosphorus tribromide In N,N-dimethyl-formamide at 0 - 20℃; for 1.5 h; 6-(Methyloxy)-1,5-naphthyridin-4-ol (21.5 g) (for a synthesis see W02007016610 Preparation 2 (a)) was stirred in DMF (150 ml) at 0°C under N2, and phosphorous tribromide (13.5 ml) was added slowly. The mixture was allowed to warm to room temperature and stirred for 90 minutes. H2O (375 ml) was added and the pH was adjusted to pH 7 by addition of solid Na2CO3. The solid was isolated by filtration with suction, dried on the sinter with suction for 2h then dried under vacuum at 45°C to give the desired compound (26.0 g, 90percent). 1H-NMR δ, ppm, DMSO-d6): 8.59 (d, 1 H), 8.30 (d, 1 H), 8.08 (d, 1H), 7.33 (d, 1 H), 4.06 (s, 3H).
90%
Stage #1: With phosphorus tribromide In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere
Stage #2: With sodium carbonate In water; N,N-dimethyl-formamide
6-(Methyloxy)-1 ,5-naphthyridin-4-ol (21.5 g) (for a synthesis see WO2007016610 Preparation 2 (a)) was stirred in DMF (150 ml) at O0C under N2, and phosphorous tribromide (13.5 ml) was added slowly. The mixture was allowed to warm to room temperature and stirred for 90 minutes. H2O (375 ml) was added and the pH was adjusted to pH 7 by addition of solid Na2CO3. The solid was isolated by filtration with suction, dried on the sinter with suction for 2h then dried under vacuum at 450C to give the desired compound (26.0 g, 90percent). 1H-NMR (δ, ppm, DMSOd6): 8.59 (d, 1 H), 8.30 (d, 1 H), 8.08 (d, 1 H), 7.33 (d, 1 H), 4.06 (s, 3H).
75%
Stage #1: With phosphorus tribromide In N,N-dimethyl-formamide at 45℃; for 0.333333 h;
Stage #2: With sodium hydroxide In water
C.
8-Bromo-2-methoxy-[1,5]naphthyridine.
To a suspension of 6-methoxy-[1,5]naphthyridin4-ol (8.8 g, 0.050 mol) in DMF (167 mL) was added PBr3 (4.7 mL, 0.050 mol) at 45° C.
The suspension became homogeneous and then a suspension formed over 20 min.
The mixture was cooled to RT and the solid was filtered and washed with Et2O (100 mL).
Further solids precipitated from the filtrate and were collected.
Water (50 mL) was added to the solid and the suspension was basified with 1 N NaOH (200 mL).
The aqueous layer was extracted with CH2Cl2 (3*250 mL), washed with brine (150 mL), dried (MgSO4) and concentrated.
The resulting residue was purified on SiO2 (0-60percent EtOAc/hexanes) to provide 8.9 g (75percent) of the title compound as a white solid. MS (ESI): exact mass calculated for C9H7BrN2O, 237.97; m/z found, 239.2 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 8.57 (d, J=4.7, 1H), 8.27 (d, J=9.0, 1H), 8.05 (d, J=4.7, 1H), 7.30 (d, J=9.0, 1H), 4.04 (s, 3H).
67%
Stage #1: With phosphorus tribromide In N,N-dimethyl-formamide at 20 - 90℃;
To a mixture of iV,iV-dimethylformamide (26.4 g, 0.36 mol ) in acetonitrile (350 mL) was added PBr3 (51.0 g, 0.188 mol) at room temperature. The mixture was stirred at 9O0C for 30 min. Then 6-methoxy-l,5-naphthyridin-4-ol (47; 22.0 g, 0.124 mol) was added and the mixture was stirred for 30 min. After cooling to room temperature, the solvent was removed in vacuo and adjusted with saturated NaHCO3 to pH=10. The precipitate was filtered and the filter cake was washed with water and dried in vacuo to give 8-bromo-2-methoxy-l,5-naphthyridine 48 (20.0 g, 0.083 mol, 67percent) as a white solid. MS calcd for C9H7BrN2O: 239.1; found: 240 [M+l]

Reference: [1] Patent: EP2080761, 2009, A1, . Location in patent: Page/Page column 15
[2] Patent: WO2010/81874, 2010, A1, . Location in patent: Page/Page column 17-18
[3] Patent: US2006/223810, 2006, A1, . Location in patent: Page/Page column 18
[4] Patent: WO2010/101949, 2010, A1, . Location in patent: Page/Page column 125
  • 5
  • [ 23443-25-6 ]
  • [ 881658-92-0 ]
YieldReaction ConditionsOperation in experiment
3.20 g With phosphorus(V) oxybromide In N,N-dimethyl-formamide at 80℃; for 0.5 h; 0004-1
Phosphorous oxybromide (5.60 g) was added to a solution of 6-methoxy-1,5-naphthyridin-4(1H)-one (3.51 g) in N,N-dimethylformamide (20 mL), followed by stirring at 80° C. for 30 minutes.
The reaction mixture was cooled to room temperature, and added dropwise to a mixture solution of methanol-water (1:10).
The resultant product was neutralized by the addition of a sodium hydroxide aqueous solution, and ethyl acetate was added thereto.
The organic layer was collected by separation, washed with a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
The obtained residue was purified by silica gel column chromatography (ethyl acetate-hexane), thereby obtaining 8-bromo-2-methoxy-1,5-naphthyridine (3.20 g) as a yellow solid.
MS m/z (M+H): 239, 241.
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 13, p. 5692 - 5703
[2] Patent: US2015/322063, 2015, A1, . Location in patent: Paragraph 0459; 0460; 0461
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 23443-25-6 ]

Ethers

Chemical Structure| 1003944-36-2

[ 1003944-36-2 ]

2,7-Dimethoxy-1,5-naphthyridine

Similarity: 0.98

Chemical Structure| 452296-79-6

[ 452296-79-6 ]

4,7-Dimethoxy-1H-pyrrolo[2,3-c]pyridine

Similarity: 0.90

Chemical Structure| 936470-68-7

[ 936470-68-7 ]

7-Methoxy-1H-pyrrolo[2,3-c]pyridin-4-ol

Similarity: 0.90

Chemical Structure| 917918-79-7

[ 917918-79-7 ]

4,7-Dimethoxy-1H-pyrrolo[2,3-c]pyridine hydrochloride

Similarity: 0.88

Chemical Structure| 642478-05-5

[ 642478-05-5 ]

3-Methoxyquinoxalin-5-ol

Similarity: 0.87

Alcohols

Chemical Structure| 936470-68-7

[ 936470-68-7 ]

7-Methoxy-1H-pyrrolo[2,3-c]pyridin-4-ol

Similarity: 0.90

Chemical Structure| 642478-05-5

[ 642478-05-5 ]

3-Methoxyquinoxalin-5-ol

Similarity: 0.87

Chemical Structure| 74668-72-7

[ 74668-72-7 ]

2-Methoxyquinolin-8-ol

Similarity: 0.85

Chemical Structure| 76052-79-4

[ 76052-79-4 ]

5-Methoxyquinoxalin-2-ol

Similarity: 0.83

Chemical Structure| 659729-61-0

[ 659729-61-0 ]

8-Methoxyquinoxalin-2-ol

Similarity: 0.83

Related Parent Nucleus of
[ 23443-25-6 ]

Naphthyridines

Chemical Structure| 1003944-36-2

[ 1003944-36-2 ]

2,7-Dimethoxy-1,5-naphthyridine

Similarity: 0.98

Chemical Structure| 1261365-35-8

[ 1261365-35-8 ]

3-Methoxy-1,5-naphthyridine

Similarity: 0.81