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

HRID 2427733Notes

Reaction equation

[F:1][CH:2]([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1.C[O:14][C:15](=O)[C:16]1[C:21]([I:22])=[CH:20][C:19]([F:23])=[CH:18][C:17]=1[CH2:24]Br.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[F:23][C:19]1[CH:18]=[C:17]2[C:16](=[C:21]([I:22])[CH:20]=1)[C:15](=[O:14])[N:9]([CH2:8][C:7]1[CH:6]=[CH:5][C:4]([O:3][CH:2]([F:12])[F:1])=[CH:11][CH:10]=1)[CH2:24]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-difluoromethoxy-benzyl amine (0.173 g, 1.0 mmol), 2-bromomethyl-4-fluoro-6-iodo-benzoic acid methyl ester (0.270 g, 0.73 mmol), and K2CO3 (0.207 g, 1.5 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-difluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.110 g, 35%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.18 (s, 2H), 4.84 (s, 2H), 6.52 (t, 1H), 7.10 (m, 3H), 7.28 (d, 2H), 7.64 (d, 1H). GC-MS: m/z 433 (M)+.

Workup

temperaturewas heated
filtrationThe resulting mixture was filtered
concentrationconcentrated

Sources & evidence

ORD record: ord-cf4ed17b52774c40800107f3034267af
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968570B2

Reaction notes

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