Hydrochloric Acid → HCID 54300597, Verbindung

HRID 1683986

Reaktionsgleichung

Reaktionsgleichung von HRID 1683986
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[CH2:13][C:14]([O:16][CH3:17])=[O:15].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[Br:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=1.Cl>C1COCC1.CN1C(=O)N(C)CCC1>[Br:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][N:8]2[C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[C:6]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[C:7]2[CH3:12])=[CH:31][CH:30]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 685274-Bromobenzyl bromideHCID 82067methyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetateHCID 3251421Potassium bis(trimethylsilyl)amide

Produkt 1

HCID 54300597HCID 54300597, VerbindungAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of ester from Step 1 (13.8 g, 59 mmol) in THF (300 mL) and DMPU (40 mL) at -78° C. was added KHMDS solution (0.64M/toluene, 95 mL, 60 mmol). The reaction mixture was warmed to 0° C. and was then recooled to -78° C., at which point a solution of 4-bromobenzyl bromide (17.0 g, 68 mmol) in THF (80 mL) was added via double-tipped needle. The reaction was allowed to warm to r.t., and was then poured into 1M HCl (500 mL). The product was extracted with Et2O and the organic phase was washed with H2O and brine. After drying (MgSO4), filtration, and removal of solvent, the crude product was purified by flash chromatography (1:20 EtOAc/toluene). The resulting prodeuct was recrystallized from CH2Cl2 /hexane to give 11.4 g of the title compound.

Aufarbeitung

  1. customwas then recooled to -78° C., at which point
  2. additionwas added via double-tipped needle
  3. temperatureto warm to r.t.
  4. extractionThe product was extracted with Et2O
  5. washthe organic phase was washed with H2O and brine
  6. customAfter drying
  7. filtration(MgSO4), filtration, and removal of solvent
  8. customthe crude product was purified by flash chromatography (1:20 EtOAc/toluene)
  9. customThe resulting prodeuct was recrystallized from CH2Cl2 /hexane

Quellen und Nachweise

ORD-Eintrag
ord-5d03c8c0fcdc4883b2d09df3cd31c2d3
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05639780

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