N-Iodosuccinimide → HCID 178419453, compound

HRID 2388913Notes

Reaction equation

HRID 2388913 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.[I:11]N1C(=O)CCC1=O>ClC(Cl)C.C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([I:11])=[N:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 404274545-Bromopyrazolo[3,4-b]pyridine

Product 1

HCID 178419453HCID 178419453, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-bromo-1H-pyrazolo[3,4-b]pyridine (3.00 g, 15.2 mmol) and N-iodosuccinimide (3.60 g, 16.0 mmol) were dissolved in anhydrous dichloroethane (100 mL). The resulting mixture was stirred under reflux conditions for 6 h, cooled to room temperature and diluted with THF (300 mL). The resulting solution was washed with a saturated aqueous solution of sodium thiosulfate (100 mL) and brine, then dried over magnesium sulfate, filtered and concentrated. The residue was titurated with a 1:1 mixture of dichloromethane and ether and then ether before being dried in vacuum to afford 5-bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine (3.795 g, 77% yield) as a beige-brown solid. 1H-NMR (500 MHz, d6-DMSO) δ 14.31 (s, 1H), 8.65 (d, 1H), 8.20 (d, 1H). MS: m/z 323, 325 [MH+].

Workup

  1. washThe resulting solution was washed with a saturated aqueous solution of sodium thiosulfate (100 mL) and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionThe residue was titurated with a 1:1 mixture of dichloromethane and ether
  6. dry with materialether before being dried in vacuum

Sources & evidence

ORD record
ord-ce93dfa5f2114964ac60ca929075f6e6
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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