N-Iodosuccinimide → HCID 118071097, compound

HRID 920715Notes

Reaction equation

HRID 920715 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:23]=[C:11]3[CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C1C(=O)N([I:31])C(=O)C1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:23]([I:31])=[C:11]3[CH2:12][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:14][CH2:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 118071101HCID 118071101, compound

Product 1

HCID 118071097HCID 118071097, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Intermediate 4F (5.0 g, 15.76 mmol) in dichloromethane (25 mL) was added NIS (5.32 g, 23.63 mmol) and stirred at room temperature for 2 h. The reaction mixture was diluted with DCM and washed with water. The organic layer was dried over Na2SO4 and concentrated to afford Intermediate 4G (6 g, 86%) as colorless semi-solid which was used in the next step without any purification. MS(ES): m/z=444 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 7.61-7.66 (m, 1H), 7.56 (ddd, J=10.04, 2.51, 1.51 Hz, 1H), 7.39 (td, J=8.03, 6.02 Hz, 1H), 7.04-7.10 (m, 1H), 4.56 (bs, 2H), 4.22 (t, J=5.52 Hz, 2H), 3.92 (t, J=5.52 Hz, 2H), 1.52 (s, 9H).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-64d3d3f86afc43309e69d78aa1b14679
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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