Methyl chloroformate → Methyl 7-chlorothieno[3,2-B]pyridine-2-carboxylate

HRID 500762Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 500762
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[CH:9][S:10][C:3]=12.[Li]CCCC.Cl[C:17]([O:19][CH3:20])=[O:18]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[S:10][C:3]=12

Komponenten

5

Edukt 3

HCID 6586Methyl chloroformateHCID 112752517-Chlorothieno[3,2-b]pyridineHCID 178418339Butyllithium

Produkt 1

HCID 59424429Methyl 7-chlorothieno[3,2-B]pyridine-2-carboxylateAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 2 (7.0 g, 41.3 mmol) in anhydrous THF (100 mL) at −78° C. under a nitrogen atmosphere was added n-BuLi (24.7 mL, 2.5 M in hexanes, 61.8 mmol). After 1 hour, methyl chloroforrnate (9.6 ml, 124 mmol) was added and the reaction mixture was stirred for an extra hour at the same temperature, quenched with excess methanol and allowed to warm to room temperature. The solvent was then evaporated and the residue was purified by flash chromatography using hexane —AcOEt (70:30) as an eluent. The product from the column was re-crystallized from ethyl acetate to afford title compound 37 (4.3g, 46% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.75 (dd, J=0.8 and 4.8 Hz, 1H), 8.26 (d, J=0.8 Hz, 1H), 7.74 (dd, J=0.8 and 5.2 Hz, 1H), 3.93 (s, 3H).

Aufarbeitung

  1. customquenched with excess methanol
  2. customThe solvent was then evaporated
  3. customthe residue was purified by flash chromatography
  4. customThe product from the column was re-crystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-207df06b9c724173a6c5db3cd65710d7
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772247B2

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