Reaction #1135831

ord-da8d10456f154bfaadf1d0d11749c3e7

Reaction equation

COC(=O)CCCCCCC(=O)Nc1ccc(Br)cc1N
methyl 8-(2-amino-4-bromophenylamino)-8-oxooctanoate
CC(=O)O
acetic acid
COC(=O)CCCCCCc1nc2cc(Br)ccc2[nH]1
methyl 7-(5-bromo-1H-benzimidazol-2-yl)heptanoate
Yield 84.3%

Solvents

Conditions

Temperature
110°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Concentrationconcentrated
  2. 2
    OtherThe residue was purified by biotage column chromatography

Procedure

To a solution of methyl 8-(2-amino-4-bromophenylamino)-8-oxooctanoate (140 mg, 0.395 mmol) in toluene was added a drop of acetic acid. The reaction was heated to 110° C. overnight and concentrated. The residue was purified by biotage column chromatography to give methyl 7-(5-bromo-1H-benzimidazol-2-yl)heptanoate (113 mg)

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09381196B2uspto-grants-2016_07