Potassium Iodide → 2-{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione

HRID 1914607Notes

Reaction equation

HRID 1914607 reaction equation
[OH:1][N:2]=[C:3]([C:10]1[N:14]([CH3:15])[N:13]=[N:12][N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].Br[CH2:25][C:26]1[N:31]=[C:30]([N:32]2[C:40](=[O:41])[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:33]2=[O:42])[CH:29]=[CH:28][CH:27]=1>C(#N)C.O>[CH3:15][N:14]1[C:10]([C:3](=[N:2][O:1][CH2:25][C:26]2[N:31]=[C:30]([N:32]3[C:33](=[O:42])[C:34]4[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:40]3=[O:41])[CH:29]=[CH:28][CH:27]=2)[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[N:11][N:12]=[N:13]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 112323512-(6-Bromomethyl-pyridin-2-YL)-isoindole-1,3-dioneHCID 135990939N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

Product 1

HCID 866565682-{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dioneYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (21.5 g, 0.106 mol) in acetonitrile (638 mL) was added cesium carbonate (72.4 g, 0.222 mol), potassium iodide (1.76 g, 0.011 mol) and then 2-[6-(bromomethyl)pyridin-2-yl]-1H-isoindole-1,3(2H)-dione (35.23 g, 0.111 mol), the white slurry was stirred at room temperature for four hours at room temperature. Water (700 mL) was added, the precipitate was filtered off and washed with water until colourless, then dried in vacuo overnight to yield to of 2-{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione [40.0 g; 86% of theory; HPLC/MS: m/z=440 (M+H); log P(HCOOH)=3.04].

Workup

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

Sources & evidence

ORD record
ord-321684fa4f374f59a79b954ef3acb930
Source dataset
uspto-grants-2013_12
Patent number
US08614217B2

Reaction notes

Loading…