Cesium carbonate → 2-bromo-6-(6-tert-butyl-1-oxophthalazin-2(1H)-yl)benzaldehyde

HRID 1644211

Reaktionsgleichung

Reaktionsgleichung von HRID 1644211
Br[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:3]=1[CH:4]=[O:5].[C:11]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[NH:20][N:19]=[CH:18]2)([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[Cs+].[Cs+].COC1C2C(=C3C(=CC=2)C(OC)=CC=N3)N=CC=1>[Cu]I.O1CCOCC1>[Br:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([N:20]2[N:19]=[CH:18][C:17]3[C:22](=[CH:23][CH:24]=[C:15]([C:11]([CH3:13])([CH3:12])[CH3:14])[CH:16]=3)[C:21]2=[O:25])[C:3]=1[CH:4]=[O:5]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 104622984,7-Dimethoxy-1,10-phenanthrolineHCID 126486412,6-DibromobenzaldehydeHCID 576339336-(tert-butyl)phthalazin-1(2H)-one

Produkt 1

HCID 580161852-bromo-6-(6-tert-butyl-1-oxophthalazin-2(1H)-yl)benzaldehydeAusbeute 69,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

5.90 g (22.4 mmol) of 2,6-dibromobenzaldehyde, 1.80 g (8.90 mmol) of 6-tert-butyl-2H-phthalazin-1-one, 6.02 g (18.5 mmol) of cesium carbonate, 179 mg (0.940 mmol) of copper(I) iodide, and 428 mg (1.87 mmol) of 4,7-dimethoxy-1,10-phenanthroline were weighed into a 100 mL reaction flask fitted with a stir bar and septum cap. Added 50 mL of anhydrous dioxane. Purged the reaction mixture with nitrogen for 15 min. Stirred at 100° for 18 h. Partitioned the reaction mixture between 200 mL of 10% MeOH/CH2Cl2 and 200 mL of water. Separated phases and extracted the aqueous phase with 2×100 mL of 10% MeOH/CH2Cl2. The combined organic extracts were washed with 200 mL of brine, dried over Na2SO4, and the solvent was removed on rotavap. Purified the crude by flash chromatography on silica gel to obtain 2.37 g of the title compound as an off-white solid. MS (ESI) doublet 385, 387 (M+H)+.

Aufarbeitung

  1. customfitted with a stir bar
  2. customseptum cap
  3. customPurged the reaction mixture with nitrogen for 15 min
  4. customPartitioned the reaction mixture between 200 mL of 10% MeOH/CH2Cl2 and 200 mL of water
  5. extractionSeparated phases and extracted the aqueous phase with 2×100 mL of 10% MeOH/CH2Cl2
  6. washThe combined organic extracts were washed with 200 mL of brine
  7. dry with materialdried over Na2SO4
  8. customthe solvent was removed on rotavap
  9. customPurified the crude by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-06397d36b03640b9bc2d8b9d7efb6adb
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124604B2

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