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

HRID 2427730Notes

Reaction equation

[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1)#[N: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:2]([CH2:1][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)[CH2:22]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-cyano-benzyl amine (0.218 g, 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-cyano-benzyl)-2,3-dihydro-isoindol-1-one (0.160 g, 41%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.19 (s, 2H), 4.83 (s, 2H), 7.13 (d, 1H), 7.42 (d, 2H), 7.64 (m, 3H). GC-MS: m/z 392 (M)4.

Workup

temperaturewas heated
filtrationThe resulting mixture was filtered
concentrationconcentrated

Sources & evidence

ORD record: ord-f2dd4083bbe8494b9cfc5ae7c06b5312
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968570B2

Reaction notes

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