N-Iodosuccinimide → HCID 90104751, compound

HRID 1049881Notes

Reaction equation

HRID 1049881 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[CH:15]=[CH:14][NH:13][C:10]3=[N:11][CH:12]=2)=[CH:3][CH:2]=1.[I:16]N1C(=O)CCC1=O>CC(C)=O>[I:16][C:15]1[C:9]2[C:10](=[N:11][CH:12]=[C:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[N:8]=2)[NH:13][CH:14]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 90105361HCID 90105361, compound

Product 1

HCID 90104751HCID 90104751, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 22 (0.35 g) and acetone (20 mL) of acetone was added in one portion N-iodosuccinimide (0.44 g). The mixture was stirred at RT for 30 min and then concentrated to afford 0.8 g of crude material. The crude product was purified by SiO2 chromatography eluting with and EtOH/EtOAc gradient (1 to 15% over 15 minutes) to afford 0.36 g of pure 7-iodo-2-(pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazine (24).

Workup

  1. concentrationconcentrated
  2. customto afford 0.8 g of crude material
  3. customThe crude product was purified by SiO2 chromatography
  4. washeluting with and EtOH/EtOAc gradient (1 to 15% over 15 minutes)

Sources & evidence

ORD record
ord-58b569c93b6b4d5292b215fcec354392
Source dataset
uspto-grants-2016_07
Patent number
US09382257B2

Reaction notes

Loading…