Triphenylphosphine → 1-(6-Fluoro-4-((2-phenylthiazol-4-yl)methoxy)benzofuran-2-yl)ethanone

HRID 1424358Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1424358
[F:1][C:2]1[CH:13]=[C:12]([OH:14])[C:5]2[CH:6]=[C:7]([C:9](=[O:11])[CH3:10])[O:8][C:4]=2[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:34]1([C:40]2[S:41][CH:42]=[C:43]([CH2:45]O)[N:44]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.ClCCl.C1C=CC=CC=1>[F:1][C:2]1[CH:13]=[C:12]([O:14][CH2:45][C:43]2[N:44]=[C:40]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[S:41][CH:42]=2)[C:5]2[CH:6]=[C:7]([C:9](=[O:11])[CH3:10])[O:8][C:4]=2[CH:3]=1

Komponenten

8

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 27764734-(Hydroxymethyl)-2-phenyl-1,3-thiazoleHCID 867009001-(6-Fluoro-4-hydroxybenzofuran-2-yl)ethanone

Produkt 1

HCID 867008991-(6-Fluoro-4-((2-phenylthiazol-4-yl)methoxy)benzofuran-2-yl)ethanoneAusbeute 39,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 241BenzeneLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Benzene was added to 1-(6-fluoro-4-hydroxybenzofuran-2-yl)ethanone (Example 36C, 178 mgs, 0.917 mmol) and the mixture was sonicated for 30 sec. and concentrated in vacuo to remove traces of water in the starting material. Triphenylphosphine (373 mgs, 1.421 mmol) was added and the mixture was dried on high vacuum for 10 min. (2-Phenylthiazol-4-yl)methanol (Example 3B, 175 mgs, 0.917 mmol) and THF (15 mL) were added and the mixture was sonicated/heated for 5 min. Diisopropyl azodicarboxylate (275 μL, 1.412 mmol) in THF (2 mL) was added dropwise over 1 h and the resulting yellow solution was sonicated for 15 min. and stirred overnight at r.t. The mixture was diluted in dichloromethane, washed with saturated. NaHCO3, brine, dried over MgSO4 and concentrated. The residue was purified on silica gel chromatography (ISCO 24 g gold column, using 5% ethyl acetate in hexanes to 40% (10% increments)) to give the title material (132 mgs, 32%) as a white solid. LC (Method B): 2.613 min. LCMS (APCI) calcd for C20H15FNO3S [M+H]+ m/z 368.07. found 368.2. 1H NMR (CDCl3, 400 MHz) δ ppm: 7.94-8.02 (m, 2H), 7.62-7.67 (m, 1H), 7.44-7.51 (m, 3H), 7.38 (s, 1H), 6.91-6.96 (m, 1H), 6.64-6.72 (m, 1H), 5.39 (d, J=0.78 Hz, 2H), 2.58 (s, 3H).

Aufarbeitung

  1. customthe mixture was sonicated for 30 sec
  2. concentrationand concentrated in vacuo
  3. customto remove traces of water in the starting material
  4. additionwere added
  5. temperaturethe mixture was sonicated/heated for 5 min
  6. customthe resulting yellow solution was sonicated for 15 min.
  7. washwashed with saturated
  8. dry with materialNaHCO3, brine, dried over MgSO4
  9. concentrationconcentrated
  10. customThe residue was purified on silica gel chromatography (ISCO 24 g gold column, using 5% ethyl acetate in hexanes to 40% (10% increments))

Quellen und Nachweise

ORD-Eintrag
ord-04acc4d7e55445a1b3850df1752ac2aa
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927688B2

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