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(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)(1-methyl-1H-benzo[d]imidazol-2-yl)methanone → (1-methyl-1H-benzo[d]imidazol-2-yl)(4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanone

HRID 410208
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 410208
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:8]([O:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([C:22]4[N:26]([CH3:27])[C:25]5[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=5[N:23]=4)=[O:21])=[CH:16][CH:15]=3)=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1>C1COCC1.[OH-].[OH-].[Pd+2].[O-2].[O-2].[Mn+4]>[CH3:27][N:26]1[C:25]2[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=2[N:23]=[C:22]1[C:20]([C:17]1[CH:16]=[CH:15][C:14]([O:13][C:8]2[C:7]([CH:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:19][CH:18]=1)=[O:21]
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Komponenten

5

Edukt 1

HCID 59326995(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)(1-methyl-1H-benzo[d]imidazol-2-yl)methanone

Produkt 1

HCID 59326816(1-methyl-1H-benzo[d]imidazol-2-yl)(4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9942167Palladium hydroxideKatalysatorHCID 178418406HCID 178418406, VerbindungKatalysator
HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

A solution of (4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)(1-methyl-1H-benzo[d]imidazol-2-yl)methanone (0.120 g, 0.292 mmol) in THF (10 mL) was evacuated and treated with Pd(OH)2 (20 mg) under nitrogen. The reaction was stirred under a hydrogen atmosphere with a balloon. After 24 hours, the reaction was filtered through a small plug of celite and the filtrate was treated with manganese dioxide (0.254 g, 2.92 mmol). The reaction was stirred at 50° C. for 1 hour and filtered through celite. The filtered was reduced under vacuum. The residue was taken up in DCM and washed (2×) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate and purified by column chromatography on silica gel using a gradient of 30 to 80% EtOAc in hexanes to give (1-methyl-1H-benzo[d]imidazol-2-yl)(4-(3-(tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanone as a white solid. MS (ESI, pos. ion) m/z: 414.0. IC50 (uM) +++++.

Aufarbeitung

  1. filtrationthe reaction was filtered through a small plug of celite
  2. stirringThe reaction was stirred at 50° C. for 1 hour
  3. filtrationfiltered through celite
  4. washwashed (2×) with an aqueous saturated solution of sodium bicarbonate
  5. dry with materialThe organic layer was then dried with sodium sulfate
  6. custompurified by column chromatography on silica gel using a gradient of 30 to 80% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-551dbdc101074b8dbec7931746da209f
Quelldatensatz
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08759532B2

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