Potassium Carbonate → 5-Fluoro-7-iodo-2-(4-chloro-benzyl)-2,3-dihydro-isoindol-1-one

HRID 2427728Notes

Reaction equation

HRID 2427728 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.C[O:11][C:12](=O)[C:13]1[C:18]([I:19])=[CH:17][C:16]([F:20])=[CH:15][C:14]=1[CH2:21]Br.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[F:20][C:16]1[CH:15]=[C:14]2[C:13](=[C:18]([I:19])[CH:17]=1)[C:12](=[O:11])[N:7]([CH2:6][C:5]1[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:21]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 660364-ChlorobenzylamineHCID 67252371HCID 67252371, compound

Product 1

HCID 672513365-Fluoro-7-iodo-2-(4-chloro-benzyl)-2,3-dihydro-isoindol-1-oneYield 50.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-benzyl amine (1.3 mmol), 2-bromomethyl-4-fluoro-6-iodo-benzoic acid methyl ester (0.374 g, 1.0 mmol), and K2CO3 (0.277 g, 2 mmol) in toluene (4 mL) was heated with stirring at 100° C. for 2 h. The resulting mixture was filtered and concentrated. Silica gel column chromatography using 30% ethyl acetate in hexane afforded 5-fluoro-7-iodo-2-(4-chloro-benzyl)-2,3-dihydro-isoindol-1-one (0.204 g, 50%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.15 (s, 2H), 4.74 (s, 2H), 7.10 (d, 1H), 7.23-7.33 (m, 4H), 7.67 (d, 11H). GC-MS: m/z 401 (M)+.

Workup

  1. temperaturewas heated
  2. filtrationThe resulting mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e82d8d5bdca74ba695af84a175aab0d4
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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