Sodium hydride → 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carbaldehyde

HRID 1435445Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1435445
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4]1.[C:10]([C:14]1[N:18]([CH2:19][CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:17]2[CH:26]=[CH:27][C:28]([S:30](Cl)(=[O:32])=[O:31])=[CH:29][C:16]=2[N:15]=1)([CH3:13])([CH3:12])[CH3:11]>C1COCC1>[C:10]([C:14]1[N:18]([CH2:19][CH:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)[C:17]2[CH:26]=[CH:27][C:28]([S:30]([N:3]3[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4]3)(=[O:31])=[O:32])=[CH:29][C:16]=2[N:15]=1)([CH3:13])([CH3:11])[CH3:12]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 6403081H-pyrrole-3-carboxaldehydeHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Produkt 1

HCID 579373391-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carbaldehydeAusbeute 41,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

NaH (0.49 mg, 60%, 12.4 mmol) was a solution of 1H-Pyrrole-3-carbaldehyde (0.21 mg, 2.47 mmol) in THF (30 mL) at 0° C. The reaction mixture was allowed to warm to room temperature, stirred for 1 hour at room temperature and cooled down to 0° C. again. 2-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (1.1 g, 20.97 mmol) was added slowly, allowed the reaction to warm to room temperature and stirred for 1 hour. The reaction mixture was quenched with NaHCO3 (5 mL), diluted with EtOAc (100 mL), washed with brine (2×15 mL) and dried over Na2SO4. The crude product was purified by MPLC on silica gel using Hexane/EtOAc (1:1) to give 0.44 g (34%) of a white solid as the title compound. 1H NMR (400 MHz, CHLOROFORM-D) δ 1.45-1.55 (m, 4 H), 1.56 (s, 9 H), 2.16-2.31 (m, 1 H), 3.25-3.35 (m, 2 H), 3.94-4.02 (m, 2 H), 4.22 (d, J=7.42 Hz, 2 H), 6.67 (dd, J=3.42, 1.66 Hz, 1 H), 7.18-7.22 (m, 1 H), 7.44 (d, J=8.79 Hz, 1 H), 7.76-7.82 (m, 2 H) 8.36 (d, J=1.76 Hz, 1 H) 9.79 (s, 1 H); MS (ESI) (M+H)+=430.00.

Aufarbeitung

  1. customat 0° C
  2. temperaturecooled down to 0° C. again
  3. customthe reaction
  4. temperatureto warm to room temperature
  5. stirringstirred for 1 hour
  6. customThe reaction mixture was quenched with NaHCO3 (5 mL)
  7. additiondiluted with EtOAc (100 mL)
  8. washwashed with brine (2×15 mL)
  9. dry with materialdried over Na2SO4
  10. customThe crude product was purified by MPLC on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4c73697bed65483fa755b81b533b5dbf
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07615642B2

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