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Lithium Hexamethyldisilazide → 2,6-difluoro-N-[1-({2-methyl-4-[(phenylmethyl)oxy]phenyl}methyl)-1H-pyrazol-3-yl]benzamide

HRID 1946388
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1946388
[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][NH:9][N:8]=1)=[O:5].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:27]1([CH2:33][O:34][C:35]2[CH:40]=[CH:39][C:38]([CH2:41]Br)=[C:37]([CH3:43])[CH:36]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1>[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][N:9]([CH2:41][C:38]2[CH:39]=[CH:40][C:35]([O:34][CH2:33][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:36][C:37]=2[CH3:43])[N:8]=1)=[O:5]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 2733832Lithium HexamethyldisilazideHCID 667708914-(Bromomethyl)-3-methylphenyl phenylmethyl etherHCID 178522346HCID 178522346, Verbindung2×

Produkt 1

HCID 595478992,6-difluoro-N-[1-({2-methyl-4-[(phenylmethyl)oxy]phenyl}methyl)-1H-pyrazol-3-yl]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
3×

Versuchsvorschrift

To a solution of 2,6-difluoro-N-1H-pyrazol-3-ylbenzamide (for a preparation see Intermediate 9)(1.31 g, 5.87 mmol) in anhydrous THF (30 ml) was added 1.0 M lithium bis(trimethylsilyl)amide in THF (6 ml, 6 mmol) at ambient temperature under nitrogen. The yellow solution was stirred for 20 min. To the solution was added a solution of 4-(bromomethyl)-3-methylphenyl phenylmethyl ether (1.72 g, 5.91 mmol) in THF (13 ml). The mixture was stirred overnight. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (120 ml) and saturated aqueous sodium hydrogen carbonate (100 ml). The phases were separated and the aqueous phase washed with ethyl acetate (30 ml). The combined organic extracts were dried (MgSO4), filtered and the solvent removed in vacuo to leave a yellow oil (3.10 g). The residue was loaded in DCM and purified on silica (100 g) using 0-100% ethyl acetate-cyclohexane. The appropriate fractions were combined and the solvent evaporated in vacuo to give the title compound as a yellow gum (1.9 g); LCMS: (System 4) MH+=434, tRET=3.14 min.

Aufarbeitung

  1. stirringThe mixture was stirred overnight
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between ethyl acetate (120 ml) and saturated aqueous sodium hydrogen carbonate (100 ml)
  4. customThe phases were separated
  5. washthe aqueous phase washed with ethyl acetate (30 ml)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d35c897df5dd46f39d70d8f433342636
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08399436B2

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