Iodine → 2-Amino-5-bromo-3-iodopyridine

HRID 1625014Notes

Reaction equation

HRID 1625014 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[I:9]([O-])(=O)(=O)=O.[Na+].II.FC(F)(F)C(O)=O.S([O-])([O-])=O.[Na+].[Na+]>C(#N)C.O>[NH2:1][C:2]1[C:7]([I:9])=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1

Participants

8

Reactant 5

HCID 807IodineHCID 6422Trifluoroacetic acidHCID 24437Sodium SulfiteHCID 706222-Amino-5-bromopyridineHCID 23667635Sodium periodate

Product 1

HCID 15165082-Amino-5-bromo-3-iodopyridineYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-amino-5-bromopyridine (2) in acetonitrile was added sodiumperiodate (0.4 equiv) and iodine (0.65 equiv). Trifluoroacetic acid (0.65 equiv) was added over 15 min and the reaction mixture was heated at 80° C. overnight. HPLC indicated 96% conversion at this point. An aqueous solution of sodium sulfite was added, followed by more water to precipitate the product which was filtered off and washed with water. The title compound (11) was isolated as a brown crystalline solid in 75% yield. MS (Turbo Spray): 298 (M+H+, 100%)

Workup

  1. customto precipitate the product which
  2. filtrationwas filtered off
  3. washwashed with water

Sources & evidence

ORD record
ord-807c0b25fe784a97ac925e2002bce275
Source dataset
uspto-grants-2014_07
Patent number
US08779150B2

Reaction notes

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