5-FLUORO-3,4-DIHYDRO-1,8-NAPHTHYRIDIN-2(1H)-ONE
- Product Name
- 5-FLUORO-3,4-DIHYDRO-1,8-NAPHTHYRIDIN-2(1H)-ONE
- CAS No.
- 1237535-78-2
- Chemical Name
- 5-FLUORO-3,4-DIHYDRO-1,8-NAPHTHYRIDIN-2(1H)-ONE
- Synonyms
- EOS-60485;5-FLUORO-3,4-DIHYDRO-1,8-NAPHTHYRIDIN-2(1H)-ONE;1,8-Naphthyridin-2(1H)-one, 5-fluoro-3,4-dihydro-;5-fluoro-1,2,3,4-tetrahydro-1,8-naphthyridin-2-one;5-fluoro-3,4-dihydro-1,8-naphthyridin-2(1H)-one(WXFC0576);5-fluoro-1,2,3,4-tetrahydro-1,8-naphthyridin-2-one - [F81881]
- CBNumber
- CB33078346
- Molecular Formula
- C8H7FN2O
- Formula Weight
- 166.15
- MOL File
- 1237535-78-2.mol
5-FLUORO-3,4-DIHYDRO-1,8-NAPHTHYRIDIN-2(1H)-ONE Property
- Boiling point:
- 241.8±50.0 °C(Predicted)
- Density
- 1.45±0.1 g/cm3(Predicted)
- storage temp.
- under inert gas (nitrogen or Argon) at 2-8°C
- pka
- 1.90±0.20(Predicted)
- Appearance
- White to off-white Solid
- InChI
- InChI=1S/C8H7FN2O/c9-6-3-4-10-8-5(6)1-2-7(12)11-8/h3-4H,1-2H2,(H,10,11,12)
- InChIKey
- NOGFPJHXTCXVDA-UHFFFAOYSA-N
- SMILES
- N1C2C(=C(F)C=CN=2)CCC1=O
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- F598438
- Product name
- 5-Fluoro-3,4-dihydro-1,8-naphthyridin-2(1H)-one
- Packaging
- 500mg
- Price
- $310
- Updated
- 2021/12/16
- Product number
- HCH0620904
- Product name
- 5-FLUORO-1,2,3,4-TETRAHYDRO-1,8-NAPHTHYRIDIN-2-ONE
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $453.21
- Updated
- 2021/12/16
- Product number
- CD11319321
- Product name
- 5-Fluoro-3,4-dihydro-1,8-naphthyridin-2(1H)-one
- Purity
- 97%
- Packaging
- 1g
- Price
- $465
- Updated
- 2021/12/16
- Product number
- 1237535782
- Product name
- 5-Fluoro-3,4-dihydro-1,8-naphthyridin-2(1H)-one
- Packaging
- 5g
- Price
- $1447.2
- Updated
- 2021/12/16
- Product number
- 1237535782
- Product name
- 5-Fluoro-3,4-dihydro-1,8-naphthyridin-2(1H)-one
- Packaging
- 25g
- Price
- $4112.79
- Updated
- 2021/12/16
5-FLUORO-3,4-DIHYDRO-1,8-NAPHTHYRIDIN-2(1H)-ONE Chemical Properties,Usage,Production
Synthesis
3054-95-3
1237535-77-1
1237535-78-2
Step 3: Preparation of 5-fluoro-3,4-dihydro-1,8-naphthyridin-2(1H)-one A round bottom flask was charged with tert-butyl (4-fluoro-3-iodopyridin-2-yl)carbamate (20.0 g, 59.2 mmol), 3,3-diethoxy-1-propene (13.5 mL, 88.7 mmol), DMF (150 mL), water (50 mL), DIPEA (15.4 mL, 88.7 mmol) and Pd catalyst 1 ( Corma, A.; Garcia, H.; Leyva, A. Tetrahedron 61, 9848, 2005) (480 mg, 0.827 mmol). The reaction mixture was stirred in an oil bath at 140 °C for 5 hours. After completion of the reaction, the mixture was cooled in a refrigerator for 2 days. The precipitate was separated by filtration, washed with ether and dried to give 3.25 g of pink colored needle-like crystals. The filtrate was concentrated to give a slightly reddish semi-solid. The substance was redissolved in DCM and the solution was allowed to pass through a 200 g silica gel column. The resulting solution was concentrated to give a red/orange residue, which was recrystallized from 2-propanol (150 mL) to give 9.4 g of pink solid. The pink solid was further purified by column chromatography (silica gel, eluting with a 0-75% EtOAc/DCM gradient) to give 1.41 g of white powder. The total product was 4.66 g in 47% yield. LC/MS: (FA) ES+ 167. 1H NMR (300 MHz, d6-DMSO): δ 10.67 (s, 1H), 8.13-8.08 (m, 1H), 6.93-6.88 (m, 1H), 2.87 (t, 2H), 2.51 (t, 2H). Note: This reaction can also be performed under the same conditions using Pd(OAc)2 as a catalyst with the ligand tri-o-tolylphosphine or no ligand. A similar method can be used for the preparation of 5-chloro-3,4-dihydro-1,8-naphthyridin-2(1H)-one from 2,4-dichloropyridine. LC/MS: (AA) ES+ 183. 1H NMR (400 MHz, d6-DMSO): δ 10.68 (s, 1H), 8.07-8.06 (m, 1H), 7.13-7.11 (m, 1H), 2.96 (t, 2H), 2.55 (t, 2H).
References
[1] Patent: US2010/197924, 2010, A1. Location in patent: Page/Page column 11-12
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 6, p. 1836 - 1846
[3] Patent: WO2011/146591, 2011, A1. Location in patent: Page/Page column 76
[4] Patent: US2012/15942, 2012, A1. Location in patent: Page/Page column 54
5-FLUORO-3,4-DIHYDRO-1,8-NAPHTHYRIDIN-2(1H)-ONE Preparation Products And Raw materials
Raw materials
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