N-Iodosuccinimide → N-(3-(3-iodo-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide

HRID 531435Notes

Reaction equation

HRID 531435 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([C:10]3[CH:11]=[C:12]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:13]=[CH:14][CH:15]=3)[CH:9]=[C:4]2[CH:3]=[CH:2]1.[I:21]N1C(=O)CCC1=O>CC(C)=O>[I:21][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[C:8]([C:10]3[CH:11]=[C:12]([NH:16][S:17]([CH3:20])(=[O:18])=[O:19])[CH:13]=[CH:14][CH:15]=3)[CH:9]=2)[NH:1][CH:2]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 58087575N-(3-(1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide

Product 1

HCID 90031153N-(3-(3-iodo-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamideYield 50%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Using similar reaction conditions as described in step i of intermediate 1, N-(3-(1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide (800 mg, 3 mmol) was iodinated with N-iodo succinimide (764 mg, 3 mmol) in acetone (5 ml) to afford 600 mg (50% yield) of the pure product. LCMS: m/z=413.4 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-ed80769ce66b491fada4a6f01f5bd4db
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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