Bromine → HCID 66904813, compound

HRID 1691649Notes

Reaction equation

HRID 1691649 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[CH:4][N:3]=1.C([O-])(=O)C.[Na+].[Br:20]Br>C(O)(=O)C.ClCCl>[NH2:1][C:2]1[C:7]([Br:20])=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 225048025-(4-Fluorophenyl)pyridin-2-amine

Product 1

HCID 66904813HCID 66904813, compoundYield 105.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-5-(4-fluorophenyl)pyridine (0.80 g, 4.25 mmol) in 20 ml glacial acetic acid was added sodium acetate (1.39 g, 17.0 mmol). Subsequently, a solution of bromine (0.44 mL, 8.50 mmol) in 2 ml glacial acetic acid was added dropwise to the reaction by addition funnel. After the addition, the reaction was heated to reflux for 1 hour then cooled and diluted with dichloromethane. The solution was washed with 25 ml saturated aqueous sodium hydrogen sulfate and then 25 ml water then dried over magnesium sulfate and concentrated to a brown oil. Automated purification on a silica gel ISCO column (120 g column, 2.5% MeOH—CH2Cl2) gave 1.20 g (60%) of 2-amino-3-bromo-5-(4-fluorophenyl)pyridine as an off-white/pink solid.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction was heated
  3. temperatureto reflux for 1 hour
  4. temperaturethen cooled
  5. washThe solution was washed with 25 ml saturated aqueous sodium hydrogen sulfate
  6. dry with material25 ml water then dried over magnesium sulfate
  7. concentrationconcentrated to a brown oil
  8. custompurification on a silica gel ISCO column (120 g column, 2.5% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-9303d36da37a435fad396cdb27558d98
Source dataset
uspto-grants-2012_04
Patent number
US08153804B2

Reaction notes

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