Methanesulfonyl chloride → Ethyl 2-methyl-4-{[1-(methylsulfonyl)azetidin-3-yl]oxy}-1-benzofuran-6-carboxylate

HRID 1177300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1177300
[NH:1]1[CH2:4][CH:3]([O:5][C:6]2[C:11]3[CH:12]=[C:13]([CH3:15])[O:14][C:10]=3[CH:9]=[C:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:7]=2)[CH2:2]1.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH3:15][C:13]1[O:14][C:10]2[CH:9]=[C:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:7]=[C:6]([O:5][CH:3]3[CH2:4][N:1]([S:22]([CH3:21])(=[O:24])=[O:23])[CH2:2]3)[C:11]=2[CH:12]=1

Komponenten

4

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 59560268Ethyl 4-(azetidin-3-yloxy)-2-methyl-1-benzofuran-6-carboxylate

Produkt 1

HCID 59560425Ethyl 2-methyl-4-{[1-(methylsulfonyl)azetidin-3-yl]oxy}-1-benzofuran-6-carboxylateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of ethyl 4-(azetidin-3-yloxy)-2-methyl-1-benzofuran-6-carboxylate (324b) (200 mg, 0.73 mmol) in DCM containing TEA (0.4 mL, 2.9 mmol) was added methanesulfonyl chloride (0.07 mL, 0.87 mmol). The mixture was stirred at room temperature for 2 hrs. The reaction was diluted with DCM, washed with NaHCO3, brine, dried over Na2SO4 and concentrated under reduced pressure. The product was purified via gradient silica gel chromatography using EtOAc/Hexanes (10/90 to 30/70) to provide the product (206 mg, 80%) as a white solid after evaporation of the solvents. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.34-1.51 (m, 3 H) 2.49 (s, 3 H) 2.89-3.07 (m, 3 H) 4.06-4.22 (m, J=9.23, 4.33 Hz, 2 H) 4.33-4.54 (m, 4 H) 5.07-5.23 (m, 1 H) 6.52 (s, 1 H) 7.02 (s, 1 H) 7.82 (s, 1 H); MS (ESI, pos): 354.

Aufarbeitung

  1. washwashed with NaHCO3, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe product was purified via gradient silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8a46483407984b10abb874504bd9f0fc
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842713B2

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