Potassium Carbonate → [3-(4-{1,2-Dimethyl-1-[5-(pyridin-2-ylmethoxy)pyridin-2-yl]propyl}phenyl)-1,2,4-oxadiazol-5-yl]methanol

HRID 1644871Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1644871
C(=O)([O-])[O-].[K+].[K+].C([O:10][CH2:11][C:12]1[O:16][N:15]=[C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([CH3:41])([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=4)=[CH:29][N:28]=3)[CH:24]([CH3:26])[CH3:25])=[CH:19][CH:18]=2)[N:13]=1)(=O)C.C(=O)(O)[O-].[Na+]>O.CO>[CH3:41][C:23]([C:20]1[CH:21]=[CH:22][C:17]([C:14]2[N:13]=[C:12]([CH2:11][OH:10])[O:16][N:15]=2)=[CH:18][CH:19]=1)([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=2)=[CH:29][N:28]=1)[CH:24]([CH3:26])[CH3:25]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 57910807[3-(4-{1,2-Dimethyl-1-[5-(pyridin-2-ylmethoxy)pyridin-2-yl]propyl}phenyl)-1,2,4-oxadiazol-5-yl]methyl acetate

Produkt 1

HCID 57910795[3-(4-{1,2-Dimethyl-1-[5-(pyridin-2-ylmethoxy)pyridin-2-yl]propyl}phenyl)-1,2,4-oxadiazol-5-yl]methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Potassium carbonate (743 mg, 5.38 mmol) in water (1.00 mL) was added to a stirred solution of 3c (0.896 mmol) in MeOH (3.00 mL) at rt. After approximately 1 h, the reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic extracts were washed with water, brine, dried (sodium sulfate) and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-6% MeOH/DCM as eluent) to furnish the title compound 3d. m/z (ES) 431 (MH)+. 1HNMR (500 MHz, CD3OD): δ 8.55 (d, 1H, J=3.3 Hz), 8.28 (d, 1H, J=2.7 Hz), 7.94 (d, 2H, J=8.5 Hz), 7.88 (dt, 1H, J=1.7, 7.7 Hz), 7.61 (d, 1H, J=7.8 Hz), 7.48 (d, 2H, J=8.5 Hz), 7.35 (m, 3H), 5.23 (s, 2H), 3.08 (m, 1H, J=6.6 Hz), 1.70 (s, 3H), 0.86 (d, 3H, J=6.6 Hz), 0.80 (d, 3H, J=6.6 Hz).

Aufarbeitung

  1. extractionextracted three times with EtOAc
  2. washThe combined organic extracts were washed with water, brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash chromatography on silica gel (gradient elution; 0%-6% MeOH/DCM as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-ccded3786a774244bab76ec22351288f
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124628B2

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