2-(Dimethylamino)ethanol → 5-(2-Dimethylamino-ethoxy)-7-methyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one

HRID 2427721Notes

Reaction equation

HRID 2427721 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.[CH3:25][N:26]([CH3:30])[CH2:27][CH2:28][OH:29].C([O-])([O-])=O.[Cs+].[Cs+].C(Cl)(Cl)Cl.CO>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:25][N:26]([CH3:30])[CH2:27][CH2:28][O:29][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

7

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 10796Cesium carbonateHCID 11560384HCID 11560384, compoundHCID 21584188Chloroform methanol

Product 1

HCID 579496355-(2-Dimethylamino-ethoxy)-7-methyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-oneYield 25%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromo-7-methyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.078 g, 0.2 mmol), 2-dimethylamino-ethanol (0.04 mL, 0.4 mmol), Pd(OAc)2 (0.001 g, 0.004 mmol), and Cs2CO3 (0.130 g, 0.4 mmol) in toluene (3 mL) was stirred at 100° C. for 24 h. Workup and silica gel column chromatography using 5:1 CHCl3-MeOH afforded 5-(2-dimethylamino-ethoxy)-7-methyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.020 g, 25%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.32 (s, 6H), 2.70 (m, 5H), 4.06 (t, 2H), 4.18 (s, 2H), 4.74 (s, 2H), 6.70 (d, 2H), 7.15-7.37 (m, 4H).

Sources & evidence

ORD record
ord-3b0c96f741b740bc8407bbefe5a8116b
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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