1-(4-iodophenyl)-2-methyl-1H-imidazole → (2SR,4RS)-4-cyano-2-methyl-4-[3-[4-(2-methylimidazol-1-yl) phenylthio]phenyl]-3,4,5,6-tetrahydro-2H-pyran

HRID 1418494

Reaktionsgleichung

Reaktionsgleichung von HRID 1418494
[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10](I)=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.[C:14]([C:16]1([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([S:29][Si](C(C)C)(C(C)C)C(C)C)[CH:24]=2)[CH2:21][CH2:20][O:19][CH:18]([CH3:22])[CH2:17]1)#[N:15].CC(C)([O-])C.[K+]>C(O)C.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>[C:14]([C:16]1([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([S:29][C:10]3[CH:11]=[CH:12][C:7]([N:3]4[CH:4]=[CH:5][N:6]=[C:2]4[CH3:1])=[CH:8][CH:9]=3)[CH:24]=2)[CH2:21][CH2:20][O:19][CH:18]([CH3:22])[CH2:17]1)#[N:15]

Komponenten

6

Edukt 3

HCID 112890901-(4-iodophenyl)-2-methyl-1H-imidazoleHCID 18786333(2SR,4RS)-4-cyano-2-methyl-4-(3-triisopropylsilylthiophenyl)-3,4,5,6-tetrahydro-2H-pyranHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 18786347(2SR,4RS)-4-cyano-2-methyl-4-[3-[4-(2-methylimidazol-1-yl) phenylthio]phenyl]-3,4,5,6-tetrahydro-2H-pyranAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-(2-methylimidazol-1-yl)phenyl iodide (1.21 g, 3.1 mmol) and (2SR, 4RS)-4-cyano-2-methyl-4-(3-triisopropylsilylthiophenyl)-3,4,5,6-tetrahydro-2H-pyran (795 mg, 2.8 mmol) in ethanol (20 ml) was added tetrakis(triphenylphosphine)palladium(0) (215 mg, 0.2 mmol) and potassium tert-butoxide (383 mg, 3.4 mmol) under a nitrogen atmosphere. The resulting mixture was heated at reflux temperature for 15.5 h, then cooled and concentrated in vacuo. The residue was diluted in ethyl acetate (100 ml), and washed with water (2×100 ml), brine (100 ml) and dried (MgSO4) and concentrated. Purification by silica-gel column chromatography, eluting with dichloromethane-methanol (25:1), gave 1.01 g (93%) of the titled compound as a yellow gum.

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux temperature for 15.5 h
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted in ethyl acetate (100 ml)
  6. washwashed with water (2×100 ml), brine (100 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customPurification by silica-gel column chromatography
  10. washeluting with dichloromethane-methanol (25:1)

Quellen und Nachweise

ORD-Eintrag
ord-851c65ac56834088ae7e98a9775e0812
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05883106

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