Vinyl ether → 1-[5-Benzyloxy-7-(1-ethoxyvinyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea

HRID 712286Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 712286
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](Br)[C:12]2[S:16][C:15]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:14][C:13]=2[CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:30]([O:32][CH2:33][CH3:34])=[CH2:31])CCC.C(OC=C)=C>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:30]([O:32][CH2:33][CH3:34])=[CH2:31])[C:12]2[S:16][C:15]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:14][C:13]=2[CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 8024Vinyl etherHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 578136291-(5-Benzyloxy-7-bromo-benzothiazol-2-yl)-3-ethyl-urea

Produkt 1

HCID 866639991-[5-Benzyloxy-7-(1-ethoxyvinyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

1-(5-benzyloxy-7-bromo-1,3-benzothiazol-2-yl)-3-ethyl-urea (1 g, 2.46 mmol) and tributyl-(1-ethoxy-vinyl)-stannane (1.77 g, 4.92 mmol) were dissolved in DMF (30 mL) and the mixture deoxygenated by bubbling N2 through the solution for 20 min. Pd(PPh3)4, (284 mg, 0.246 mmol) was added and the reaction heated to 100° C. for 4 h under a N2 atmosphere, at the end of which time LCMS indicated clean formation of the vinyl ether. The reaction was concentrated under reduced pressure, diluted with EtOAc, washed with water then brine and the organic layer dried (MgSO4), filtered and the solvent removed in vacuo to give the desired compound.

Aufarbeitung

  1. customthe mixture deoxygenated
  2. customby bubbling N2 through the solution for 20 min
  3. concentrationThe reaction was concentrated under reduced pressure
  4. additiondiluted with EtOAc
  5. washwashed with water
  6. dry with materialbrine and the organic layer dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6274cc00a01c4548bb0bda619ffba435
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181234B2

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