Sodium Acetate → HCID 11535765, Verbindung

HRID 1919643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1919643
Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9]C)=O.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O.C([O-])(=O)C.[Na+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[S:3]1[C:2]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[NH:11][C:7](=[O:9])[C:6]=2[CH:5]=[CH:4]1

Komponenten

6

Edukt 3

HCID 517045Sodium AcetateHCID 2773216(2-Aminophenyl)boronic acidHCID 53302196Methyl 2-bromothiophene-3-carboxylate

Produkt 1

HCID 11535765HCID 11535765, VerbindungAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

In a microwave vessel, methyl 2-bromo-3-thiophene carboxylate (1.0 eq, 64 mg, 0.29 mmol), 2-amino phenyl boronic acid (1.2 eq, 48 mg, 0.35 mmol), sodium acetate (3.0 eq, 71 mg, 0.86 mmol) and PdCl2(dppf) (0.1 eq, 15 mg, 0.028 mmol) were mixed together in anhydrous DMF (0.2 ml). The mixture was heated in a microwave oven at 120° C. for 5 nm. The material was purified by preparative HPLC. Acetonitrile was evaporated, and the compound was extracted with CH2Cl2 (3×). The combined extracts were washed with water, dried over Na2SO4, and the solvents removed in vacuo. Recrystallization in EtOH provided thieno[3,2-c]quinolin-4(5H)-one as a tan crystalline solid (7 mg, 12% yield). LCMS (ES): 95% pure, m/z 202 [M+1]+; 1H NMR (CDCl3/CD3OD, 9:1, 400 MHz) δ 7.28 (m, 1H), 7.33 (m, 1H), 7.43-7.50 (m, 2H), 7.74 (d, J=4.4, 1H), 7.82 (d, J=7.6, 1H) ppm.

Aufarbeitung

  1. customThe material was purified by preparative HPLC
  2. customAcetonitrile was evaporated
  3. extractionthe compound was extracted with CH2Cl2 (3×)
  4. washThe combined extracts were washed with water
  5. dry with materialdried over Na2SO4
  6. customthe solvents removed in vacuo
  7. customRecrystallization in EtOH

Quellen und Nachweise

ORD-Eintrag
ord-5c592b9cdc154bc5b0f330db9ba85cf6
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08168651B2

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