2-(Dimethylamino)ethanol → HCID 57949738, compound

HRID 2427722Notes

Reaction equation

HRID 2427722 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:7](=[O:15])[N:6]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1)[CH2:5]2.[CH3:28][N:29]([CH3:33])[CH2:30][CH2:31][OH:32].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]>[CH3:28][N:29]([CH3:33])[CH2:30][CH2:31][O:32][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:7](=[O:15])[N:6]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1)[CH2:5]2

Participants

7

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 10796Cesium carbonateHCID 21584188Chloroform methanolHCID 866299795-Bromo-2-(4-trifluoromethoxy-benzyl)-7-trifluoromethyl-2,3-dihydro-isoindol-1-one

Product 1

HCID 57949738HCID 57949738, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromo-7-trifluoromethyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.123 g, 0.3 mmol), 2-dimethylamino-ethanol (0.05 mL, 0.5 mmol), Pd(OAc)2 (0.002 g, 0.006 mmol), and Cs2CO3 (0.195 g, 0.6 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)-2-(4-trifluoromethoxy-benzyl)-7-trifluoromethyl-2,3-dihydro-isoindol-1-one (0.050 g, 36%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.35 (s, 6H), 2.73 (t, 2H), 4.13 (t, 2H), 4.23 (s, 2H), 4.74 (s, 2H), 7.04-7.38 (m, 6H).

Sources & evidence

ORD record
ord-f119713340ff4a50a40efc135a8cf723
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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