Ammonium Chloride → 2-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-3-(1-hydroxy-2-propynyl)-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097456Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2097456
[CH:1]1([O:4][C:5]2[CH:6]=[C:7]([C:15]3[N:32]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:18]4[CH:19]=[N:20][N:21]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:22](=[O:23])[C:17]=4[C:16]=3[CH:41]=[O:42])[CH:8]=[CH:9][C:10]=2[O:11][CH:12]([F:14])[F:13])[CH2:3][CH2:2]1.[C:43]([Mg]Br)#[CH:44].[Cl-].[NH4+]>O1CCCC1>[CH:1]1([O:4][C:5]2[CH:6]=[C:7]([C:15]3[N:32]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:18]4[CH:19]=[N:20][N:21]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:29])[CH3:30])[C:22](=[O:23])[C:17]=4[C:16]=3[CH:41]([OH:42])[C:43]#[CH:44])[CH:8]=[CH:9][C:10]=2[O:11][CH:12]([F:13])[F:14])[CH2:2][CH2:3]1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 86627032HCID 86627032, VerbindungHCID 178418486HCID 178418486, Verbindung

Produkt 1

HCID 866270332-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-3-(1-hydroxy-2-propynyl)-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To 25 ml of tetrahydrofuran solution containing 1.01 g (1.62 mmol) of 2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-3-formyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in the same manner as in Example 15-(a) was added dropwise 3.6 ml of tetrahydrofuran solution containing 0.5M ethynyl magnesium bromide at 60° C., and the mixture was stirred at the same temperature for 30 minutes. After completion of the reaction, the reaction mixture was poured into a saturated ammonium chloride solution, and extracted with toluene. The organic layer after separation was washed successively with water, and then, with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=7:3 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 1.11 g of the title compound as a yellowish oil. (Yield: 96%)

Aufarbeitung

  1. customobtained in the same manner as in Example 15-(a)
  2. customAfter completion of the reaction
  3. extractionextracted with toluene
  4. customThe organic layer after separation
  5. washwas washed successively with water
  6. dry with materialwith a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionthe fractions containing the desired compound
  9. concentrationwere concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fb70c8c60d094baeabbc19f295851194
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450319B2

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