Cesium carbonate → 2-Chloro-4-methoxy-3-(tetrahydro-pyran-2-yloxymethyl)-pyridine

HRID 1959610Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1959610
[Cl:1][C:2]1[C:7]([CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)=[C:6](F)[CH:5]=[CH:4][N:3]=1.BrC1C=NC=C(Cl)C=1[CH2:24][O:25]C1CCCCO1.C([O-])([O-])=O.[Cs+].[Cs+]>CO>[Cl:1][C:2]1[C:7]([CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)=[C:6]([O:25][CH3:24])[CH:5]=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 44190473HCID 44190473, VerbindungHCID 866453642-Chloro-4-fluoro-3-(tetrahydro-pyran-2-yloxymethyl)-pyridine

Produkt 1

HCID 866453632-Chloro-4-methoxy-3-(tetrahydro-pyran-2-yloxymethyl)-pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-chloro-4-fluoro-3-(tetrahydro-pyran-2-yloxymethyl)-pyridine (0.20 g. 0.81 mmol) which was prepared according to the synthesis of 3-bromo-5-chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridine in anhydrous MeOH (4 mL) was added Cs2CO3 (0.54 g. 1.6 mmol). After vigorous stirring for 20 h at room temperature acedic acid (92 μL. 1.6 mmol) was added the solvent was removed in vacuo and the residue was partitioned between DCM (20 mL) and water (4 mL). The organic layer was dried over Na2SO4 filtered and concentrated in vacuo. The resulting title compound was used for the next reaction without purification. MS (m/z): 257.9 [M+H+].

Aufarbeitung

  1. additionwas added the solvent
  2. customwas removed in vacuo
  3. customthe residue was partitioned between DCM (20 mL) and water (4 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting title compound was used for the next reaction without purification

Quellen und Nachweise

ORD-Eintrag
ord-08b5f9dc8262426c8a69112e9dc8110e
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410134B2

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