Dimethylformamide → 5-Methoxy-7-iodo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one

HRID 2427744Notes

Reaction equation

HRID 2427744 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([I: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.C[O-].[Na+].CO.CN([CH:33]=[O:34])C.C(OCC)(=O)C>CCCCCC>[I:11][C:9]1[CH:10]=[C:2]([O:34][CH3:33])[CH:3]=[C:4]2[C:8]=1[C:7](=[O:12])[N:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]([F:22])([F:23])[F:24])=[CH:16][CH:15]=1)[CH2:5]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 23694274Sodium methanolate methanolHCID 579496155-Fluoro-7-iodo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one

Product 1

HCID 579493525-Methoxy-7-iodo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-oneYield 31%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-fluoro-7-iodo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.226 g, 0.5 mmol), 30% sodium methoxide-methanol (0.7 mL) and DMF (0.12 mL) was stirred at 100° C. for 1 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 7-iodo-5-methoxy-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.071 g, 31%). 1H NMR (300 MHz, CDCl3): δ (ppm) 3.83 (s, 3H), 4.12 (s, 2H), 4.75 (s, 2H), 6.87 (bs, 1H), 7.17 (d, 2H), 7.33 (d, 2H), 7.44 (bs, 1H). GC-MS: m/z 463 (M)+, 394 (M−69)+, 378 (M−85)+.

Sources & evidence

ORD record
ord-c3370d2c274d4895a40d745ec2669933
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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