Potassium Carbonate → 1-Boc-2-[4-(1,1-dioxidoisothiazolidin-2-yl)phenyl]-6-methoxyindole

HRID 506109Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 506109
[C:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][C:18](F)(F)F)[CH:15]=2)[CH:10]=[C:9]1B(O)O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].I[C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH2:36][CH2:35][CH2:34][S:33]2(=[O:38])=[O:37])=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>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]>[C:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[CH:10]=[C:9]1[C:26]1[CH:27]=[CH:28][C:29]([N:32]2[CH2:36][CH2:35][CH2:34][S:33]2(=[O:38])=[O:37])=[CH:30][CH:31]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 147632212-(4-Iodophenyl)isothiazolidine-1,1-dioxideHCID 57355675(1-(tert-Butoxycarbonyl)-6-(trifluoromethoxy)-1H-indol-2-yl)boronic acid

Produkt 1

HCID 594306781-Boc-2-[4-(1,1-dioxidoisothiazolidin-2-yl)phenyl]-6-methoxyindole

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

To a mixture of 1-Boc-6-trifluoromethoxyindole-2-boronic acid prepared above (0.74 g, 2.1 mmol), 2-(4-iodophenyl)isothiazolidine-1,1-dioxide (0.76 g, 2.4 mmol), and PdCl2(dppf) (0.08 g, 0.1 mmol) in DMF (6.0 mL), is added K2CO3 solution (3.2 mL, 2.0 M, 6.4 mmol). The mixture is stirred at room temperature overnight and then poured into ice-water (100 mL). The precipitate is collected and washed with water and purified by flash column chromatography (silica gel, DCM/EtOAc, 9/1) to furnish 1-Boc-2-[4-(1,1-dioxidoisothiazolidin-2-yl)phenyl]-6-methoxyindole, which is treated with 50% TFA in DCM (15 mL) at room temperature for 1 h. After the removal of the volatiles, the residue is carefully stirred with saturated NaHCO3 for 0.5 h. The precipitate is collected via filtration and washed thoroughly with water and dried to provide essentially pure 1-H-2-[4-(1,1-dioxidoisothiazolidin-2-yl)phenyl]-6-trifluoromethoxyindole.

Aufarbeitung

  1. customThe precipitate is collected
  2. washwashed with water
  3. custompurified by flash column chromatography (silica gel, DCM/EtOAc, 9/1)

Quellen und Nachweise

ORD-Eintrag
ord-fae868d810be4b12948cee1c2132e507
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781478B2

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