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

HRID 2427729Notes

Reaction equation

HRID 2427729 reaction equation
[CH2:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1)[CH3:2].C[O:12][C:13](=O)[C:14]1[C:19]([I:20])=[CH:18][C:17]([F:21])=[CH:16][C:15]=1[CH2:22]Br.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[F:21][C:17]1[CH:16]=[C:15]2[C:14](=[C:19]([I:20])[CH:18]=1)[C:13](=[O:12])[N:8]([CH2:7][C:6]1[CH:9]=[CH:10][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=1)[CH2:22]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 38702194-ethylbenzylamineHCID 67252371HCID 67252371, compound

Product 1

HCID 672516105-Fluoro-7-iodo-2-(4-ethyl-benzyl)-2,3-dihydro-isoindol-1-oneYield 47%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-ethyl-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-ethyl-benzyl)-2,3-dihydro-isoindol-1-one (0.184 g, 47%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.20 (t, 3H), 2.65 (q, 2H), 4.16 (s, 2H), 4.74 (s, 2H), 7.10 (d, 1H), 7.23-7.33 (m, 4H), 7.63 (d, 1H). GC-MS: m/z 395 (M)+.

Workup

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

Sources & evidence

ORD record
ord-c6922548f2e24fc39e36f974793c676c
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

Loading…