Cesium carbonate → HCID 86635674, compound

HRID 2427723Notes

Reaction equation

HRID 2427723 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[C:7](=O)[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]1[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][OH:34])[CH2:28][CH2:27]1.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]>[CH3:11][C:9]1[CH:10]=[C:2]([O:34][CH2:33][CH2:32][N:29]2[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]2)[CH:3]=[C:4]2[C:8]=1[CH2:7][N:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]([F:23])([F:22])[F:24])=[CH:16][CH:15]=1)[CH2:5]2

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 2311841-(2-Hydroxyethyl)-4-methylpiperazineHCID 11560384HCID 11560384, compoundHCID 21584188Chloroform methanol

Product 1

HCID 86635674HCID 86635674, compoundYield 18.5%

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 (0.120 g, 0.3 mmol), 2-(4-methyl-piperazin-1yl)-ethanol (0.074 mL, 0.6 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 7-methyl-5-[2-(4-methyl-piperazin-1-yl)-ethoxy]-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-lone (0.025 g, 18%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.49 (bs, 8H), 2.75 (s, 3H), 2.83 (t, 2H), 4.16 (m, 5H), 4.73 (s, 2H), 6.70 (d, 2H), 7.13-7.37 (m, 4H).

Sources & evidence

ORD record
ord-e0ccddd3854c432f80bf8ae231007676
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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