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

HRID 2427727Notes

Reaction equation

[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1.C[O:15][C:16](=O)[C:17]1[C:22]([I:23])=[CH:21][C:20]([F:24])=[CH:19][C:18]=1[CH2:25]Br.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[F:24][C:20]1[CH:19]=[C:18]2[C:17](=[C:22]([I:23])[CH:21]=1)[C:16](=[O:15])[N:9]([CH2:8][C:7]1[CH:10]=[CH:11][C:4]([O:3][C:2]([F:12])([F:13])[F:1])=[CH:5][CH:6]=1)[CH2:25]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-trifluoromethoxy-benzyl amine (0.092 mL, 0.6 mmol), 2-bromomethyl-4-fluoro-6-iodo-benzoic acid methyl ester (0.181 g, 0.49 mmol), and K2CO3 (0.138 g, 1 mmol) in toluene 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-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.080 g, 36%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.19 (s, 2H), 4.79 (s, 2H), 7.06-7.38 (m, 5H), 7.67 (d, 1H). GC-MS: m/z 451 (M)+, 382 (M−69)+.

Workup

temperaturewas heated
filtrationThe resulting mixture was filtered
concentrationconcentrated

Sources & evidence

ORD record: ord-4832175de6504fdf98f0f9f778a40255
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968570B2

Reaction notes

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