7-Chloro-5-(3-dimethylamino-prop-1-ynyl)-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one → 7-Chloro-5-(3-dimethylamino-propyl)-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one

HRID 2427665Notes

Reaction equation

HRID 2427665 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:24]#[C:25][CH2:26][N:27]([CH3:29])[CH3:28])[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1)[CH2:7]2.[H][H].C(Cl)(Cl)Cl.CO>C(O)C.[C].[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:24][CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][C:20]([F:21])([F:22])[F:23])=[CH:17][CH:18]=1)[CH2:7]2

Participants

6

Reactant 3

HCID 115825947-Chloro-5-(3-dimethylamino-prop-1-ynyl)-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-oneHCID 21584188Chloroform methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 579497127-Chloro-5-(3-dimethylamino-propyl)-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-oneYield 50%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7-chloro-5-(3-dimethylamino-prop-1-ynyl)-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.102 g, 0.24 mmol) and 10% palladium-carbon (0.015 g) in ethanol (25 mL) was reduced under 45 p.s.i. hydrogen. Workup and silica gel column chromatography using 5:1 CHCl3-MeOH afforded 7-chloro-5-(3-dimethylamino-propyl)-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.050 g, 50%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.84 (m, 2H), 2.4 (s, 6H), 2.48 (t, 2H), 2.72 (t, 2H), 4.22 (s, 2H), 4.76 (s, 2H), 7.15-7.39 (m, 6H).

Sources & evidence

ORD record
ord-94d1a8a7714b480697b18e54e9e2807d
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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