Reacción #542527

ord-372c3afab6454fbdbf20bd30ce76ba95

Ecuación de reacción

CC(C)(C)OC(=O)N1CCC[C@@H]2c3c(O)cccc3CC[C@@H]21
cis-10-hydroxy-2,3,4a,5,6,10b-hexahydro-1H-benzo[f]quinoline-4-carboxylic acid tert-butyl ester
Cc1ccc(Cl)nn1
3-chloro-6-methyl-pyridazine
O=C([O-])[O-].[Cs+].[Cs+]
cesium carbonate
CN1CCCC1=O
N-methylpyrrolidinone
→
Cc1ccc(Oc2cccc3c2[C@H]2CCCN(C(=O)OC(C)(C)C)[C@H]2CC3)nn1
title compound
Cc1ccc(Oc2cccc3c2[C@H]2CCCN(C(=O)OC(C)(C)C)[C@H]2CC3)nn1
cis-10-(6-methyl-pyridazin-3-yloxy)-2,3,4a,5,6,10b-hexahydro-1H-benzo[f]quinoline-4-carboxylic acid tert-butyl ester

Reactantes

CC(C)(C)OC(=O)N1CCC[C@@H]2c3c(O)cccc3CC[C@@H]21
cis-10-hydroxy-2,3,4a,5,6,10b-hexahydro-1H-benzo[f]quinoline-4-carboxylic acid tert-butyl ester
Cc1ccc(Cl)nn1
3-chloro-6-methyl-pyridazine
O=C([O-])[O-].[Cs+].[Cs+]
cesium carbonate
CN1CCCC1=O
N-methylpyrrolidinone

Reactivos

Ninguno

Disolventes

CCOC(C)=O
ethyl acetate

Condiciones de reacción

Temperatura
150°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaAfter cooling to room temperature
  2. 2
    Lavadowashed with water and brine
  3. 3
    Secadodried (Na2SO4)
  4. 4
    OtroThe solvent is evaporated
  5. 5
    Otrothe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 3:1→1:2)

Procedimiento

A mixture of cis-10-hydroxy-2,3,4a,5,6,10b-hexahydro-1H-benzo[f]quinoline-4-carboxylic acid tert-butyl ester (0.40 g), 3-chloro-6-methyl-pyridazine (0.13 g), cesium carbonate (0.35 g), and N-methylpyrrolidinone (5 mL) is stirred at 150° C. for 1.5 h. After cooling to room temperature, the mixture is diluted with ethyl acetate and washed with water and brine and dried (Na2SO4). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 3:1→1:2) to give the title compound. Yield: 0.14 g (impure); LC (method 1): tR=4.19 min; Mass spectrum (ESI+): m/z=396 [M+H]+.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08497281B2uspto-grants-2013_07