Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Iodine | HCID 807 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Sodium Sulfite | HCID 24437 | — |
| Reactant | 2-Amino-5-bromopyridine | HCID 70622 | — |
| Reactant | Sodium periodate | HCID 23667635 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 2-Amino-5-bromo-3-iodopyridine | HCID 1516508 | 75% |
Reaction Steps
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%)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08779150B2 |
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| Source dataset | uspto-grants-2014_07 |
|---|
| ORD ID | ord-807c0b25fe784a97ac925e2002bce275 |
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| Source note | uspto-grants-2014_07 |
|---|
