Bromine → HCID 66617822, compound

HRID 911094Notes

Reaction equation

HRID 911094 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 room 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 ethyl 5-(2-amino-5-bromopyridin-4-yloxy)-4,6-dimethylnicotinate (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-484f9d9530ce4746ab60f846ba9ee5ba
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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