Reacción #595406

ord-18e15086be174c9f8d516389483ad5f3

Ecuación de reacción

N
NH3
Brc1ccc2c(c1)c1cc(Br)ccc1n2CC1CO1
3,6-dibromo-9-(oxiran-2-ylmethyl)-9H-carbazole
NCC(O)Cn1c2ccc(Br)cc2c2cc(Br)ccc21
white solid
Rendimiento 65.4%
NCC(O)Cn1c2ccc(Br)cc2c2cc(Br)ccc21
1-amino-3-(3,6-dibromo-9H-carbazol-9-yl)propan-2-ol
Rendimiento 65.4%

Condiciones de reacción

Temperatura
100°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe vial was tightly sealed
  2. 2
    OtroVolatile components were removed under vacuum
  3. 3
    Filtraciónthe white precipitate was filtered
  4. 4
    OtroCH2Cl2 was removed under vacuum

Procedimiento

A solution of NH3 (9.4 mL of 7M in MeOH, 65.6 mmol) was added to 3,6-dibromo-9-(oxiran-2-ylmethyl)-9H-carbazole (0.500 g, 1.31 mmol). The vial was tightly sealed and the reaction mixture was heated to 100° C. and stirred for 1 hour. Volatile components were removed under vacuum. The residue was suspended in CH2Cl2 and the white precipitate was filtered. The filtrate was saved and CH2Cl2 was removed under vacuum to afford 0.3413 g white solid as crude product, which contained about 50% unidentified side-product. This crude product was used as is in next step without any further purification. Purification by flash chromatography on silica gel provided pure material.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09095572B2uspto-grants-2015_08