tert-Butyl acetate → Tert-butyl 3-(5-chloro-1-methyl-1h-indol-2-yl)-3-oxopropanoate

HRID 1818631Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1818631
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:11]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])[CH3:12].[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25]([CH3:29])[C:24]([C:30](OCC)=[O:31])=[CH:23]2>C1COCC1>[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25]([CH3:29])[C:24]([C:30](=[O:31])[CH2:12][C:11]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:23]2

Komponenten

5

Edukt 3

HCID 10908tert-Butyl acetateHCID 2733832Lithium HexamethyldisilazideHCID 3911003Ethyl 5-chloro-1-methyl-1H-indole-2-carboxylate

Produkt 1

HCID 91475479Tert-butyl 3-(5-chloro-1-methyl-1h-indol-2-yl)-3-oxopropanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a cooled (−78° C.) solution of LHMDS (20.1 mL, 1.0 M in THF, 20.1 mmol) in THF (10 mL), was added tert-butyl acetate (2.71 mL, 20.1 mmol). After 30 min, a solution of the title compound of Example 11 Step A (1.59 g, 6.7 mmol) in THF (10 mL) was added. After 30 min, the reaction mixture was placed in a 0° C. bath, and was stirred at this temperature for 3 h, whereupon it was quenched by addition of sat. aq. NaHCO3. The aqueous phase was extracted with EtOAc, and the organic phase was concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 30%, then 30 to 100% EtOAc in hexanes) provided the title compound: LCMS C, tr=2.38 min, m/z 252.2 [M−tBu+H]+; 1H NMR (500 MHz, CDCl3) δ 7.66 (d, J=2.0 Hz, 1H), 7.34 (dd, J=9.0, 2.0 Hz, 1H), 7.31 (d, J=9.0 Hz, 1H), 7.21 (s, 1H), 4.06 (s, 3H), 3.87 (s, 2H), 1.49 (s, 9H).

Aufarbeitung

  1. waitAfter 30 min
  2. customwas placed in a 0° C.
  3. customwas quenched by addition of sat. aq. NaHCO3
  4. extractionThe aqueous phase was extracted with EtOAc
  5. concentrationthe organic phase was concentrated in vacuo
  6. customPurification by flash chromatography on silica gel (0 to 30%

Quellen und Nachweise

ORD-Eintrag
ord-c061c8c54bfa430eb9e86e3dd5ad7ef7
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598398B2

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