Réaction #68340

ord-5bfec063a8974500a36e692c56931387

Équation de réaction

CCOC(=O)c1ccc2c(C=O)c(C(C)C)[nH]c2c1
ethyl3-formyl-2-isopropyl-1H-indole-6-carboxylate
CCOC(=O)c1ccc2c(C=O)c(C(C)C)[nH]c2c1
Compound 34
CCOC(=O)c1ccc2c(C=O)c(C(C)C)[nH]c2c1
ethyl3-formyl-2-isopropyl-1H-indole-6-carboxylate
O=C([O-])[O-].[K+].[K+]
K2CO3
BrCc1ccccn1
2-(bromomethyl)pyridine
→
CCOC(=O)c1ccc2c(C=O)c(C(C)C)n(Cc3ccccn3)c2c1
title compound
CCOC(=O)c1ccc2c(C=O)c(C(C)C)n(Cc3ccccn3)c2c1
Ethyl 3-Formyl-2-isopropyl-1-(pyridin-2-ylmethyl)-1H-indole-6-carboxylate

Réactifs

CCOC(=O)c1ccc2c(C=O)c(C(C)C)[nH]c2c1
ethyl3-formyl-2-isopropyl-1H-indole-6-carboxylate
CCOC(=O)c1ccc2c(C=O)c(C(C)C)[nH]c2c1
Compound 34
CCOC(=O)c1ccc2c(C=O)c(C(C)C)[nH]c2c1
ethyl3-formyl-2-isopropyl-1H-indole-6-carboxylate
O=C([O-])[O-].[K+].[K+]
K2CO3
BrCc1ccccn1
2-(bromomethyl)pyridine

Réactifs

Aucun

Solvants

CCOC(C)=O
EtOAc
CN(C)C=O
DMF

Conditions de réaction

Température
60°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Lavagewashed with H2O, brine
  2. 2
    Séchagedried over Na2SO4
  3. 3
    Concentrationconcentrated in vacuo
  4. 4
    AutreThe residue was purified by chromatography on silica gel (0→35% EtOAc-hexanes)

Mode opératoire

Following General Procedure C, ethyl3-formyl-2-isopropyl-1H-indole-6-carboxylate (Compound 34, 278 mg, 1.07 mmol) in DMF (15 ml) was added K2CO3 (590 mg, 4.28 mmol) and 2-(bromomethyl)pyridine (914 mg, 5.35 mmol). The reaction was stirred at 60° C. for 5 h, diluted with EtOAc, washed with H2O, brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→35% EtOAc-hexanes) to yield the title compound as a yellow oil.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08524917B2uspto-grants-2013_09