N-Iodosuccinimide → HCID 178433771, compound

HRID 1914847Notes

Reaction equation

HRID 1914847 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[N:13]=[CH:12][C:11]3[CH:10]=[C:9]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:8](=[O:20])[NH:7][C:6]=3[N:5]2[N:21]=1.[I:22]N1C(=O)CCC1=O>CN(C=O)C>[I:22][C:3]1[C:2]([CH3:1])=[N:21][N:5]2[C:6]3[C:11](=[CH:10][C:9]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)=[C:8]([OH:20])[N:7]=3)[CH:12]=[N:13][C:4]=12

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 136133166HCID 136133166, compound

Product 1

HCID 178433771HCID 178433771, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Compound [IV] (0.2 g, 0.73 mmol, 1 eq.) in DMF (10 mL) was added N-iodosuccinimide (0.18 g, 0.8 mmol, 1.1 eq.) and the mixture stirred for 2 hours and concentrated. The residue was purified by silica gel chromatography using CHCl3/MeOH (10%) as eluant to give Compound [XCVII]: LCMS ink 403 (M+H); 1H NMR (400 MHz, DMSO-d6) δ ppm 7.33-7.40 (m, 1H) 7.44 (t, J=7.42 Hz, 2H) 7.69 (d, J=7.22 Hz, 2H) 8.37 (s, 1H) 8.83 (s, 1H).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel chromatography
  3. customto give Compound [XCVII]

Sources & evidence

ORD record
ord-3df0fb74f0c24e8abc8d3cc53805844f
Source dataset
uspto-grants-2013_12
Patent number
US08614221B2

Reaction notes

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