N-Iodosuccinimide → HCID 90104537, compound

HRID 1049882Notes

Reaction equation

HRID 1049882 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[N:7]=[C:8]3[CH:14]=[CH:13][NH:12][C:9]3=[N:10][CH:11]=2)[CH:3]=[N:2]1.C1C(=O)N([I:22])C(=O)C1>CC(C)=O>[I:22][C:14]1[C:8]2[C:9](=[N:10][CH:11]=[C:6]([C:4]3[CH:5]=[N:1][NH:2][CH:3]=3)[N:7]=2)[NH:12][CH:13]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 90105293HCID 90105293, compound

Product 1

HCID 90104537HCID 90104537, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 28 (0.27 g) and acetone (20 mL) was added in one portion NIS (0.36 g). The mixture was stirred at RT for 30 min and then concentrated to afford 0.55 g of crude material which was purified by SiO2 chromatography using an EtOH/EtOAc gradient (1 to 15% EtOH over 15 min) to afford 0.29 g of pure 7-iodo-2-(1H-pyrazol-4-yl)-5H-pyrrolo[2,3-b]pyrazine (30).

Workup

  1. concentrationconcentrated
  2. customto afford 0.55 g of crude material which
  3. customwas purified by SiO2 chromatography
  4. customan EtOH/EtOAc gradient (1 to 15% EtOH over 15 min)

Sources & evidence

ORD record
ord-52b4700567d34e349ed8f9cb1c8910b0
Source dataset
uspto-grants-2016_07
Patent number
US09382257B2

Reaction notes

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