Tetrahydrofuran → 1-[5-(2,6-dimethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-3-methyl-butan-1-ol

HRID 602542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602542
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5](CC)[C:4]=1[C:11]1[CH:12]=[C:13]2[C:19]([CH:20]=[O:21])=[CH:18][N:17]([C:22]3[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][CH:23]=3)[C:14]2=[CH:15][N:16]=1)C.[CH2:31]([Mg]Cl)[CH:32]([CH3:34])[CH3:33].[NH4+].[Cl-].[CH2:39]1COCC1>>[CH3:1][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:39])[C:4]=1[C:11]1[CH:12]=[C:13]2[C:19]([CH:20]([OH:21])[CH2:31][CH:32]([CH3:34])[CH3:33])=[CH:18][N:17]([C:22]3[CH:27]=[CH:26][C:25]([CH:28]([CH3:29])[CH3:30])=[CH:24][CH:23]=3)[C:14]2=[CH:15][N:16]=1

Komponenten

5

Edukt 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 866240795-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridine-3-carbaldehydeHCID 178418368HCID 178418368, Verbindung

Produkt 1

HCID 671523991-[5-(2,6-dimethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-3-methyl-butan-1-ol

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 5-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridine-3-carbaldehyde (50 mg, 0.13 mmol, prepared by the procedure described in Example 11, Step 3) in THF (2 mL) at −78° C., iso-butylmagnesium chloride (1M solution in THF, 300 μL, 0.32 mmol) is added. The mixture is stirred at −78° C. for two hours and is subsequently allowed to warm to room temperature. A saturated aqueous NH4Cl solution (5 mL) is added, and THF is removed under reduced pressure. The product is extracted with EtOAc. The combined organic extracts are washed with brine, dried over Na2SO4, and concentrated under reduced pressure. Chromatography of the residue affords 1-[5-(2,6-dimethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-3-methyl-butan-1-ol as colorless oil. 1H NMR: (CDCl3) 8.97 (s, 1H), 7.64 (s, 1H), 7.9 (s, 1H), 7.48 (d, J=120 Hz, 2H), 7.41 (d, J=10 Hz, 2H), 7.29 (t, J=10 Hz, 1H), 7.15 (d, J=12 Hz, 2H), 5.13 (m, 1H), 3.95 (m, 1H), 2.44 (m, 4H), 1.34 (d, J=14 Hz, 6H), 1.04 (t, J=10 Hz, 6H); LCMS m/z 455.34 (2.58 min).

Aufarbeitung

  1. customat −78° C.
  2. temperatureto warm to room temperature
  3. customTHF is removed under reduced pressure
  4. extractionThe product is extracted with EtOAc
  5. washThe combined organic extracts are washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7fcf7ee75d784288916e4c28eea30789
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906528B2

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