Water → (+/-)-2a,6-Dimethyl-1,2,2a,5-tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-one

HRID 551095Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 551095
Br[C:2]1[C:11]2[NH:10][C:9](=[O:12])[CH2:8][C:7]3([CH3:15])[CH2:13][NH:14][C:5]([C:6]=23)=[CH:4][CH:3]=1.[C:16](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1.O>C1COCC1.O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:15][C:7]12[CH2:13][NH:14][C:5]3[C:6]1=[C:11]([C:2]([CH3:16])=[CH:3][CH:4]=3)[NH:10][C:9](=[O:12])[CH2:8]2

Komponenten

8

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 57955363(+/-)-6-Bromo-2a-methyl-1,2,2a,5-tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-one

Produkt 1

HCID 57663733(+/-)-2a,6-Dimethyl-1,2,2a,5-tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of (±)-6-bromo-2a-methyl-1,2,2a,5-tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-one from Step B (48 mg, 0.18 mmol), tetrakis(triphenylphosphine)palladium(0) (22 mg, 0.019 mmol), potassium carbonate (75 mg, 0.54 mmol), and trimethylboroxine (0.126 mL of a 50 wt. % solution in THF, 0.50 mmol) in 1,4-dioxane (0.9 mL) and H2O (0.1 mL) was heated at 120° C. in a microwave reactor for 40 min. The cooled reaction mixture was quenched with H2O (5 mL) and extracted with EtOAc (20 mL). The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:0 to 90:10, to give the title compound. MS: m/z=203 (M+1).

Aufarbeitung

  1. customThe cooled reaction mixture
  2. customwas quenched with H2O (5 mL)
  3. extractionextracted with EtOAc (20 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with a gradient of CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-8d7ab0b9bcc84c69b276f34649487d49
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947677B2

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