Iodine → HCID 91379151, Verbindung

HRID 857369Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 857369
II.Br[CH:4]=[CH:5][CH3:6].[CH3:7][O:8][C:9](=[O:26])[CH2:10][CH:11]1[C:15]2=[CH:16][C:17]3[C:18](Br)=[CH:19][C:20]([O:23][CH3:24])=[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:26])[CH2:10][CH:11]1[C:15]2=[CH:16][C:17]3[C:18]([C:5]([CH3:6])=[CH2:4])=[CH:19][C:20]([O:23][CH3:24])=[CH:21][C:22]=3[N:14]2[CH2:13][CH2:12]1

Komponenten

8

Edukt 3

HCID 807IodineHCID 115331-Bromo-1-propeneHCID 58760742HCID 58760742, Verbindung

Produkt 1

HCID 91379151HCID 91379151, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23938PalladiumKatalysatorHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 10421208Zinc bromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To Mg (143 mg, 5.8 mmol) in THF (4 mL) with trace of I2 was added α-bromopropene (583 μL) in order to maintain a 60° C. exotherm. After 30 minutes, a solution of ZnBr2 (1.31 g, 5.8 mmol) in THF (4 mL) was added. The reaction mixture was heated at 55° C. for 1 hour, cooled to r.t. and (Pd (dppf) CH2Cl2 (50 mg) was added followed by CuI (18.5 mg). After 5 minutes a solution of methyl (8-bromo-6-methoxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (Example 22, Step 5, 200 mg, 0.59 mmol) in THF (7 mL) was added and the mixture was refluxed for 1 hour, cooled, 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 (50 mg).

Aufarbeitung

  1. temperatureThe reaction mixture was heated at 55° C. for 1 hour
  2. temperaturecooled to r.t.
  3. temperaturethe mixture was refluxed for 1 hour
  4. temperaturecooled
  5. customquenched 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-0854fb48adbd470db0cf99307948342c
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144913B2

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