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Thionyl Chloride → [2-(2,5-Dichloro-phenoxy)-5-fluoro-pyridin-3-yl]-(2-methyl-3,4-dihydro-2H-quinolin-1-yl)-methanone

HRID 1877369
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1877369
[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:3]=1[O:4][C:5]1[N:13]=[CH:12][C:11]([F:14])=[CH:10][C:6]=1[C:7]([OH:9])=O.S(Cl)(Cl)=O.C(N(C(C)C)C(C)C)C.[CH3:33][CH:34]1[CH2:43][CH2:42][C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[NH:35]1>>[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:3]=1[O:4][C:5]1[C:6]([C:7]([N:35]2[C:36]3[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:42][CH2:43][CH:34]2[CH3:33])=[O:9])=[CH:10][C:11]([F:14])=[CH:12][N:13]=1
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Komponenten

5

Edukt 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 962892-Methyl-1,2,3,4-tetrahydroquinolineHCID 673674432-(2,5-Dichloro-phenoxy)-5-fluoro-nicotinic acid

Produkt 1

HCID 46195423[2-(2,5-Dichloro-phenoxy)-5-fluoro-pyridin-3-yl]-(2-methyl-3,4-dihydro-2H-quinolin-1-yl)-methanoneAusbeute 22,2 %

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A solution of 2-(2,5-dichloro-phenoxy)-5-fluoro-nicotinic acid (36.3 mg, 0.12 mmol, 1.0 equiv) in thionyl chloride (492 mg, 300 μL, 4.14 mmol, 34.5 equiv; [CAS RN 7719-09-7]) was heated to 100° C. over night. The reaction mixture was concentrated under reduced pressure, remaining thionyl chloride removed by azotropic distillation with toluene and the residue dissolved in anhydrous DMF (1 mL). To this solution was added N-ethyldiisopropylamine (155 mg, 204 μL, 1.20 mmol, 10.0 equiv; [CAS RN 7087-68-5]) and 2-methyl-1,2,3,4-tetrahydro-quinoline (22.1 mg, 0.15 mmol, 1.25 equiv; [CAS RN 1780-19-4]) and the reaction mixture heated by microwave irradiation to 120° C. for 15 min. Removal of the solvent mixture under reduced pressure and purification by preparative HPLC on reversed phase (Xterra® PrepMSC 18, 5 μm, 19×50 mm column equipped with a Gilson Liquid Handler 215 autosampler, two Rainin Dynamax® SD-300 pumps, a Sedex ELSD 75 lightscatter and a Dionex UVD 340S UV detector) eluting with a gradient of acetonitrile/water provided 11.5 mg (22%) of the title compound. MS (ISP): 430.8 [M+H]+.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customremoved by azotropic distillation with toluene
  3. dissolutionthe residue dissolved in anhydrous DMF (1 mL)
  4. customRemoval of the solvent mixture
  5. customunder reduced pressure and purification by preparative HPLC on reversed phase (Xterra® PrepMSC 18, 5 μm, 19×50 mm column
  6. customequipped with a Gilson Liquid Handler 215 autosampler, two Rainin Dynamax® SD-300 pumps
  7. washa Sedex ELSD 75 lightscatter and a Dionex UVD 340S UV detector) eluting with a gradient of acetonitrile/water

Quellen und Nachweise

ORD-Eintrag
ord-03c3832f6bb144f8b193b916c5ec1f59
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08309734B2

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