Reacción #42499

ord-986f12927c2143d6a3c663c2a48c33dd

Ecuación de reacción

COC(=O)c1ccc2cc[nH]c2c1
Methyl 1H-indole-6-carboxylate
CC(C)(C)[O-].[K+]
potassium tert-butoxide
CCCCI
Iodobutane
CCCCn1ccc2ccc(C(=O)OC)cc21
methyl 1-butyl-1H-indole-6-carboxylate

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.STIRRINGto stir for three additional hours
  2. 2
    OtroThe mixture was partitioned between ethyl acetate and water and brine
  3. 3
    Secadodried over sodium sulfate
  4. 4
    Filtraciónfiltered
  5. 5
    Concentraciónconcentrated

Procedimiento

Methyl 1H-indole-6-carboxylate (4.17 g) was dissolved in DMSO (30 mL), and potassium tert-butoxide (2.93 g) was added. The mixture was stirred for ten min at room temperature. Iodobutane (3.0 mL) was added. The mixture was allowed to stir for three additional hours. The mixture was partitioned between ethyl acetate and water and brine, dried over sodium sulfate, filtered, and concentrated to give methyl 1-butyl-1H-indole-6-carboxylate (4.53 g). MS (ESI+) for C14H17NO2+H1 m/z 232.12 (M+H)+.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07727997B2uspto-grants-2010_06