Ethyl Acetate → 2-{3-[4-(4-Fluoro-phenoxy)-phenyl]-propyl}-7-iodo-2,3-dihydro-isoindol-1-one

HRID 2427620Notes

Reaction equation

CO[C:3](=[O:13])[C:4]1[C:9]([I:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11]Br.[F:14][C:15]1[CH:31]=[CH:30][C:18]([O:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][NH2:29])=[CH:22][CH:21]=2)=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[F:14][C:15]1[CH:31]=[CH:30][C:18]([O:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][N:29]3[CH2:11][C:5]4[C:4](=[C:9]([I:10])[CH:8]=[CH:7][CH:6]=4)[C:3]3=[O:13])=[CH:22][CH:21]=2)=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-bromomethyl-6-iodo-benzoic acid methyl ester (0.245 g, 0.7 mmol), 3-[4-(4-fluoro-phenoxy)phenyl]-propylamine (0.193 g, 0.8 mmol), and K2CO3 (0.207 g, 1.5 mmol) in toluene (5 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 2-{3-[4-(4-fluoro-phenoxy)-phenyl]-propyl}-7-iodo-2,3-dihydro-isoindol-1-one (0.086 g, 25%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.01 (m, 2H), 2.65 (t, 2H), 3.67 (t, 2H), 4.26 (s, 2H), 6.84-7.42 (m, 10H), 7.90 (d, 1H). GC-MS: m/z 487 (M)+.

Workup

temperaturewas heated

Sources & evidence

ORD record: ord-5abf36376ab24b329c479ddd22c2914a
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968570B2

Reaction notes

Loading…