Bromine → HCID 67486270, compound

HRID 1972169Notes

Reaction equation

HRID 1972169 reaction equation
[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:16]Br.C([O-])(=O)C.[NH4+]>C(O)(=O)C>[Br:16][C:14]1[C:9]([O:8][C:7]2[C:2]([CH3:1])=[N:3][CH:4]=[CH:5][CH:6]=2)=[CH:10][C:11]([NH2:15])=[N:12][CH:13]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 517165Ammonium AcetateHCID 67486234HCID 67486234, compound

Product 1

HCID 67486270HCID 67486270, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 4-(2-methylpyridin-3-yloxy)pyridin-2-amine (3.67 g, 18.2 mmol) in acetic acid (50 mL) was added bromine (0.94 ml, 18.2 mmol). The reaction was stirred at ambient temperature for 5 minutes. Ammonium acetate (1.41 g, 18.2 mmol) was added. After 5 minutes, the solution was concentrated and saturated sodium bicarbonate solution was added. The reaction was extracted with ethyl acetate, dried and concentrated to give the title compound (5.0 g, 98% yield) as light yellow solid.

Workup

  1. waitAfter 5 minutes
  2. concentrationthe solution was concentrated
  3. additionsaturated sodium bicarbonate solution was added
  4. extractionThe reaction was extracted with ethyl acetate
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c6e23e855a5d42a1ae87bb5e322905d3
Source dataset
uspto-grants-2013_04
Patent number
US08431713B2

Reaction notes

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