Sodium hydride → 1H-Benzimidazole, 2-(2,6-difluorophenyl)-1-((2,6-difluorophenyl)methyl)-

HRID 2182080

Reaktionsgleichung

Reaktionsgleichung von HRID 2182080
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=1.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=1[C:26]1C=CC=CC=1CBr.[H-].[Na+]>C1COCC1>[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=1[CH2:26][N:13]1[C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[N:10]=[C:9]1[C:3]1[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=1[F:1]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 16536142-(2,6-difluorophenyl)-1H-benzimidazoleHCID 867579372,6-Difluorophenyl-alpha-bromotoluene

Produkt 1

HCID 4688471H-Benzimidazole, 2-(2,6-difluorophenyl)-1-((2,6-difluorophenyl)methyl)-Ausbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-(2,6-difluorophenyl)benzimidazole (Example 12) (2.00 g, 8.70 mmol) and 2,6-difluoro-α-bromo-toluene (25) (2.85 g, 160 M %), were dissolved in THF (20 mL). To this mixture, NaH (0.75 g, 215 M %) was added. After mixing for 2 hours, the reaction was quenched with MeOH and concentrated. The residue was redissolved in ethylacetate, and washed with NaHCO3 (sat. aq.) and NaCl (sat. aq.). The combined washings were dried (Na2SO4), filtered and concentrated. The crude product was recrystallized from ethylacetate/hexane (1:1) yielding white powders of 1-(2,6-difluorobenzyl)-2-(2,6-difluorophenyl)benzimidazole (2.62 g, 0.35 mmol, 85% yield. M.p. 145° C. 1H-NMR (300 MHz, CD2Cl2): δ 7.77 (m, 1H, H4), 7.54 (m, 1H, H4′), 7.49m, 1H, H7), 7.29 (m, 2H, H5,6), 7.24 (m, 1H, H4″), 7.08 (m, 2H, H3′, 5′), 5.82 (m, 2H, H3″, 5″), 5.30 (s, 2H, CH2PhF2).

Aufarbeitung

  1. additionAfter mixing for 2 hours
  2. customthe reaction was quenched with MeOH
  3. concentrationconcentrated
  4. dissolutionThe residue was redissolved in ethylacetate
  5. washwashed with NaHCO3 (sat. aq.) and NaCl (sat. aq.)
  6. dry with materialThe combined washings were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was recrystallized from ethylacetate/hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-b472faa513634a938d3b217b1cf168ee
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894068B2

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