Iodine → Methyl[8-isopropenyl-6-(methylsulfonyl)-2,3-dihydro-1h-pyrrolo[1,2-a]indol-1-yl]acetate

HRID 857364

Reaktionsgleichung

Reaktionsgleichung von HRID 857364
Br[CH:2]=[CH:3][CH3:4].II.[CH3:7][O:8][C:9](=[O:28])[CH2:10][CH:11]1[C:15]2=[CH:16][C:17]3[C:18](Br)=[CH:19][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:21][C:22]=3[N:14]2[CH2:13][CH2:12]1>C1COCC1.[Zn+2].[Br-].[Br-].[Pd].[Cu]I>[CH3:7][O:8][C:9](=[O:28])[CH2:10][CH:11]1[C:15]2=[CH:16][C:17]3[C:18]([C:3]([CH3:4])=[CH2:2])=[CH:19][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:21][C:22]=3[N:14]2[CH2:13][CH2:12]1

Komponenten

8

Edukt 3

HCID 807IodineHCID 115331-Bromo-1-propeneHCID 131726144Methyl[8-bromo-6-(methylsulfonyl)-2,3-dihydro-1h-pyrrolo[1,2-a]indol-1-yl]acetate

Produkt 1

HCID 90964995Methyl[8-isopropenyl-6-(methylsulfonyl)-2,3-dihydro-1h-pyrrolo[1,2-a]indol-1-yl]acetateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23938PalladiumKatalysatorHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 10421208Zinc bromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

Alpha-bromopropene (514 μL, 5.2 mmol) was added portionwise, in order to maintain 55° C. exotherm, to Mg (126 mg, 5.2 mmol) (in THF 4 mL) and a trace of iodine. The mixture was heated and stirred for 30 minutes. Dried ZnBr2 (1.16 g, 5.2 mmol) in THF (4 mL) was added and the mixture was heated at 55° C. for 1 hour. The reaction mixture was cooled to room temperature, and Pd (dppf) CH2Cl2 (19 mg) was added followed by CuI (7 mg) after a further 5 minutes. The product of Step 1 (200 mg, 0.52 mmol) in 3 ml THF was then added. The reaction mixture was heated to 75° C. for 15 minutes. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography to give the title compound (130 mg).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperaturethe mixture was heated at 55° C. for 1 hour
  3. temperatureThe reaction mixture was cooled to room temperature
  4. temperatureThe reaction mixture was heated to 75° C. for 15 minutes
  5. customThe reaction was quenched with saturated aqueous NH4Cl
  6. extractionextracted with EtOAc
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-adefbee9523c48e496956f009ebb9053
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144913B2

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