Bromine → HCID 66617822, compound

HRID 1972158Notes

Reaction equation

HRID 1972158 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH3:21])=[N:11][CH:12]=[C:13]([C:19]=2[CH3:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:5]=[CH:4][N:3]=1.[Br:22]Br>CC(O)=O>[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH3:21])=[N:11][CH:12]=[C:13]([C:19]=2[CH3:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]([Br:22])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 66617836HCID 66617836, compound

Product 1

HCID 66617822HCID 66617822, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 5-(2-aminopyridin-4-yloxy)-4,6-dimethylnicotinate (2.5 g, 8.7 mmol) in AcOH (30 mL) was charged with dropwise addition of bromine (1M in AcOH, 8.7 ml, 8.7 mmol). The solution was stirred at ambient temperature for 30 minutes. The solution was then concentrated and neutralized with saturated NaHCO3 solution. The material was then extracted with EtOAc and the organic layer was dried, and concentrated. Flash chromatography gave the title compound (1.88 g, 59%) as a yellow solid.

Workup

  1. concentrationThe solution was then concentrated
  2. extractionThe material was then extracted with EtOAc
  3. customthe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-69bf4790c70c4cfcb6372b630893136a
Source dataset
uspto-grants-2013_04
Patent number
US08431713B2

Reaction notes

Loading…