Potassium Iodide → 2-(6-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}pyridin-2-yl)-1H-isoindole-1,3(2H)-dione

HRID 1914609Notes

Reaction equation

HRID 1914609 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].Br[CH2:14][C:15]1[N:20]=[C:19]([N:21]2[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]2=[O:31])[CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C.O>[O:7]=[C:6]1[C:5]2[C:4](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3](=[O:12])[N:2]1[O:1][CH2:14][C:15]1[N:20]=[C:19]([N:21]2[C:22](=[O:31])[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:29]2=[O:30])[CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10665N-HydroxyphthalimideHCID 10796Cesium carbonateHCID 112323512-(6-Bromomethyl-pyridin-2-YL)-isoindole-1,3-dione

Product 1

HCID 670751742-(6-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}pyridin-2-yl)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A suspension of N-hydroxyphthalimide (35.0 g, 214 mmol), 2-[6-(bromomethyl)pyridin-2-yl]-1H-isoindole-1,3(2H)-dione (74.8 g, 236 mmol), cesium carbonate (146.8 g, 450 mmol) and potassium iodide (1.78 g, 10.7 mmol) in acetonitrile (350 mL) was stirred at room temperature for 18 h. Water (300 mL) was added, the precipitate was filtered off and washed with water until colourless, then dried in vacuo overnight to yield 2-(6-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}pyridin-2-yl)-1H-isoindole-1,3(2H)-dione as a colourless solid [85.0 g; 94% of theory; HPLC/MS m/z=400 (M+H); log P(HCOOH)=2.44].

Workup

  1. filtrationthe precipitate was filtered off
  2. washwashed with water until colourless,
  3. customthen dried in vacuo overnight

Sources & evidence

ORD record
ord-83fbf80a30b74f008db0b8444ee6d117
Source dataset
uspto-grants-2013_12
Patent number
US08614217B2

Reaction notes

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