Dimethylformamide → HCID 117690933, Verbindung

HRID 1503205Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1503205
I[C:2]1[N:7]=[N:6][C:5]2[O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:4]=2[CH:3]=1.[F:16][C:17]([O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]#[CH:28])=[CH:23][CH:22]=1)([F:19])[F:18].C(N(CC)CC)C.CN(C)C=O>[Cu](I)I.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C(OCC)(=O)C>[F:16][C:17]([F:18])([F:19])[O:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]#[C:28][C:2]2[N:7]=[N:6][C:5]3[O:8][C:9]4[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=4[O:11][C:4]=3[CH:3]=2)=[CH:25][CH:26]=1

Komponenten

9

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 27784941-Ethynyl-4-(trifluoromethoxy)benzeneHCID 895846403-Iodo[1,4]benzodioxino[2,3-c]pyridazine

Produkt 1

HCID 117690933HCID 117690933, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 83717Copper iodideKatalysatorHCID 178419050HCID 178419050, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a sealed reaction container were added 3-iodo[1,4]benzodioxino[2,3-c]pyridazine (200 mg) synthesized in Production Example 9 to be mentioned later, 4-ethynylphenyl trifluoromethyl ether (0.15 mL), copper iodide (6 mg), triethylamine (64 mg), bis(triphenylphosphine)palladium (II) dichloride (22 mg) and dimethylformamide (5 mL), and the mixture was stirred at 120° C. for 0.5 hr. Ethyl acetate and water were added, the organic layer was dried over anhydrous sodium sulfate, and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 3-{[4-(trifluoromethoxy)phenyl]ethynyl}[1,4]benzodioxino[2,3-c]pyridazine (100 mg).

Aufarbeitung

  1. customTo a sealed reaction container
  2. customsynthesized in Production Example 9
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationthe solvent was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-5d3a84ecd16b40b1a5150ca533ed6a41
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09212147B2

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