Bromine → Ethyl 3-(2-amino-5-bromopyridin-4-yloxy)-4-chlorobenzoate

HRID 911035Notes

Reaction equation

HRID 911035 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=2[Cl:20])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:4][N:3]=1.[Br:21]Br>C(O)(=O)C>[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=2[Cl:20])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]([Br:21])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 66617829Ethyl 3-(2-aminopyridin-4-yloxy)-4-chlorobenzoate

Product 1

HCID 66617810Ethyl 3-(2-amino-5-bromopyridin-4-yloxy)-4-chlorobenzoateYield 61.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A flask was charged with ethyl 3-(2-aminopyridin-4-yloxy)-4-chlorobenzoate (5.50 g, 18.8 mmol) and acetic acid (50 mL), and bromine (0.943 ml, 18.4 mmol) was added. The reaction was stirred at ambient temperature for 30 minutes and then concentrated. The residue was purified by silica gel column chromatography, eluting with 20%-35% ethyl acetate in hexanes to give the desired product (4.20 g, 58.9% yield) as light yellow solid.

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column chromatography
  4. washeluting with 20%-35% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-acb1015a38cd4fb2a8527bc7d186e04d
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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