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Dimethylformamide → 7-(3-Fluoro-benzyl)-4-hydroxy-2-methyl-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester

HRID 902532
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 902532
[H-].[Na+].[CH3:3][C:4]1[S:14][C:7]2[NH:8][C:9](=[O:13])O[C:11](=[O:12])[C:6]=2[CH:5]=1.[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19]Br.[CH2:24](C(CC)(C([O-])=O)C([O-])=O)[CH3:25].[C:35](=[O:38])([O-])[O-:36].[Na+].[Na+].[CH3:41]N(C=O)C>>[CH2:24]([O:36][C:35]([C:41]1[C:9](=[O:13])[N:8]([CH2:19][C:18]2[CH:21]=[CH:22][CH:23]=[C:16]([F:15])[CH:17]=2)[C:7]2[S:14][C:4]([CH3:3])=[CH:5][C:6]=2[C:11]=1[OH:12])=[O:38])[CH3:25]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 6

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 680073-Fluorobenzyl bromideHCID 69515632,2-DiethylpropanedioateHCID 138498796-methyl-1H-thieno[2,3-d][1,3]oxazine-2,4-dione

Produkt 1

HCID 59702099
7-(3-Fluoro-benzyl)-4-hydroxy-2-methyl-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester
Ausbeute 97 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium hydride (60% dispersion in mineral oil, 5.6 g, 0.140 mol) was added slowly to a solution of 6-methyl-1H-thieno[2,3-d][1,3]oxazine-2,4-dione (68) (11.07 g, 0.060 mol) in anhydrous DMF stirred under argon at 0° C. The solution was stirred for 15 minutes before adding 3-fluoro benzylbromide (7.6 mL, 0.062 mol). The solution was allowed to come at room temperature and further stirred for 3 hours. The solution was cooled to −10° C. and diethylmalonate (9.36 mL, 0.061 mol) was added slowly. The solution was heated at 110° C. (TLC control). The reaction was cooled and poured into aqueous sodium carbonate (7.7 g, 0.072 mol) solution. The aqueous solution was washed with isopropyl ether and acidified to pH 2 with dil. HCl. The solids were filtered, washed by cold water and air dried to yield 16.9 g (97%) of 7-(3-fluoro-benzyl)-4-hydroxy-2-methyl-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester (69). 1H-NMR (DMSO-d6) δ 1.30 (t, J=7.2 Hz, 3H), 2.40 (d, J=1.2 Hz, 3H), 4.32 (q, J=7.2 Hz, 2H), 5.22 (s, 2H), 7.05-7.15 (m, 4H), 7.38 (m, 1H), 13.25 m/z 362 (M+1).

Aufarbeitung

  1. stirringThe solution was stirred for 15 minutes
  2. customto come at room temperature
  3. stirringfurther stirred for 3 hours
  4. temperatureThe solution was cooled to −10° C.
  5. temperatureThe solution was heated at 110° C. (TLC control)
  6. temperatureThe reaction was cooled
  7. washThe aqueous solution was washed with isopropyl ether
  8. filtrationThe solids were filtered
  9. washwashed by cold water and air
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-7e3c2ccc48354465ab0b567df65272da
Quelldatensatz
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07365200B2

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