Reaction #1124

ord-5a04f014ea6d40c2b125f6974f5951e3

Reaction equation

Cl
hydrochloric acid
Clc1nccc(N[C@H]2CC[C@@H](c3ccccc3)CC2)c1Br
2-chloro-3-bromo-4-(cis-4-phenylcyclohexylamino)pyridine
C[O-].[Na+]
sodium methoxide
O
water
→
COc1nccc(N[C@H]2CC[C@@H](c3ccccc3)CC2)c1Br
2-Methoxy-3-bromo-4-(cis-4-phenylcyclohexylamino)pyridine

Reactants

Cl
hydrochloric acid
Clc1nccc(N[C@H]2CC[C@@H](c3ccccc3)CC2)c1Br
2-chloro-3-bromo-4-(cis-4-phenylcyclohexylamino)pyridine
C[O-].[Na+]
sodium methoxide
O
water

Reagents

None

Solvents

CN(C)C=O
dimethylformamide
CO
methanol

Conditions

Temperature
80°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureAfter cooling
  2. 2
    Extractionthe reaction product is extracted with ethyl acetate
  3. 3
    OtherFor purification it
  4. 4
    Otheris chromatographed

Procedure

2.21 g (6.04 mmol) of 2-chloro-3-bromo-4-(cis-4-phenylcyclohexylamino)pyridine in 30 ml of dimethylformamide are treated with 4.31 ml of 30% strength solution of sodium methoxide in methanol and the mixture is heated at 80° C. for 1 hour. After cooling, water is added, the mixture is adjusted to pH 8 using 1/2 conc. hydrochloric acid and the reaction product is extracted with ethyl acetate. For purification it is chromatographed. Yield: 1.72 g (79%); Rf =0.4 (diisopropyl ether)

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05723450uspto-grants-1998_03