Reacción #41991

ord-71866f818b4e40e097b0c842d5917d59

Ecuación de reacción

CCC1(c2c[nH]c3c(N)cccc23)CCc2cc(F)ccc21
3-(1-ethyl-5-fluoro-indan-1-yl)-1H-indol-7-ylamine
COC(=O)Cl
methyl chloroformate
CCC1(c2c[nH]c3c(NC(=O)OC)cccc23)CCc2cc(F)ccc21
title compound
Rendimiento 36.0%
CCC1(c2c[nH]c3c(NC(=O)OC)cccc23)CCc2cc(F)ccc21
[3-(1-Ethyl-5-fluoro-indan-1-yl)-1H-indol-7-yl]-carbamic acid methyl ester
Rendimiento 36.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Lavadowash with 1N aqueous hydrochloric acid (2×)
  2. 2
    Secadodry over anhydrous sodium sulfate
  3. 3
    Filtraciónfilter
  4. 4
    Concentraciónconcentrate solution in vacuo
  5. 5
    OtroPurify the residue on silica eluting with 0 to 75% ethyl acetate/hexanes over 30 minutes

Procedimiento

Dissolve 3-(1-ethyl-5-fluoro-indan-1-yl)-1H-indol-7-ylamine (0.35 g, 1.19 mmol) in pyridine (3 ml). Add methyl chloroformate (0.10 ml, 1.31 mmol, 1.1 equivalents) and stir at room temperature under nitrogen overnight. Dilute with ether, wash with 1N aqueous hydrochloric acid (2×), dry over anhydrous sodium sulfate, filter, and concentrate solution in vacuo. Purify the residue on silica eluting with 0 to 75% ethyl acetate/hexanes over 30 minutes to provide the title compound as a white solid (0.15 g, 36%). LC-MS m/z 353.1 (M++1).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07728150B2uspto-grants-2010_06