Sodium Iodide → 5-Iodo-7-methyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one

HRID 2427507Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[C:7](=[O:12])[N:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=1)[CH2:5]2.CN[C@@H]1CCCC[C@H]1NC.[I-:35].[Na+]>C(O)CCC.C(OCC)(=O)C.[Cu]I>[I:35][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[C:7](=[O:12])[N:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=1)[CH2:5]2

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 5-Bromo-7-methyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (300 mg, 0.713 mmol) in butanol (3 ml), (1R,2R)—N,N′-dimethylcyclohexane-1,2-diamine (20 mg, 0.142 mmol), copper(I) iodide (13.6 mg, 0.07 mmol) and sodium iodide (214 mg, 1.43 mmol) were added. The resulting mixture was stirred at 120° C. overnight. After cooling, the mixture was diluted with ethyl acetate, washed with water, brine, dried over anhydrous sodium sulphate, filtered, concentrated. Column chromatography (30% EtOAc/Hexanes) provided the title compound as a yellow oil (274 mg, 85%). 1H NMR (300 MHz, CDCl3): δ 7.55-7.57 (m, 2H), 7.30-7.35 (m, 2H), 7.16-7.20 (m, 2H), 4.74 (s, 2H), 4.318 (s, 2H), 2.69 (s, 3H).

Workup

temperatureAfter cooling
washwashed with water, brine
dry with materialdried over anhydrous sodium sulphate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-8632217d84854480afb4f9247cac44f2
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968570B2

Reaction notes

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