Dimethylformamide → Methyl benzo[d]isothiazole-5-carboxylate

HRID 1880429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1880429
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[CH:7][C:6]=2[CH:10]=1.[C:11]([O-:14])(=[O:13])C.[Na+].[CH3:16]N(C=O)C>CO.Cl[Pd]Cl>[S:9]1[C:5]2[CH:4]=[CH:3][C:2]([C:11]([O:14][CH3:16])=[O:13])=[CH:10][C:6]=2[CH:7]=[N:8]1

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 517045Sodium AcetateHCID 178424445-Bromo-1,2-benzothiazole

Produkt 1

HCID 66920624Methyl benzo[d]isothiazole-5-carboxylateAusbeute 5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24290Palladium ChlorideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1.51 g of 5-bromobenzo[d]isothiazole and 825.0 mg of 1,1′-cis(diphenylphosphino)ferrocene]dichloropalladium(II) in 35 mL methanol in a small Parr bottle was added sodium acetate (1.74 g) and DMF (543 μL). The mixture was degassed several times with nitrogen, then shaken under an atmosphere of CO (40 psi) at 50 degrees for 18 hours. The solution was filtered and concentrated. The residue was flash chromatographed (0-20% EtOAc/Haptanes gradient) to yield 61.0 mg (5%) of methyl benzo[d]isothiazole-5-carboxylate as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm 3.96 (s, 3 H) 8.17 (d, J=0.98 Hz, 2 H) 8.84 (s, 1 H) 9.08 (s, 1 H); LC-MS @ 194.1 (M+1).

Aufarbeitung

  1. customThe mixture was degassed several times with nitrogen
  2. filtrationThe solution was filtered
  3. concentrationconcentrated
  4. customchromatographed (0-20% EtOAc/Haptanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-43197e0b7fb24e1fb0bf0f0a99e00d3f
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318762B2

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