7-Chloro-5-ethynyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one → 7-Chloro-5-ethyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one

HRID 2427757Notes

Reaction equation

HRID 2427757 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:24]#[CH:25])[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(O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:24][CH3:25])[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:23])([F:21])[F:22])=[CH:17][CH:18]=1)[CH2:7]2

Participants

5

Reactant 2

HCID 579497397-Chloro-5-ethynyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 579495477-Chloro-5-ethyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-oneYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 7-chloro-5-ethynyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.080 g, 0.22 mmol) in ethanol (25 mL) was treated with 10% palladium on carbon (20 mg) and shook vigorously under 45 p.s.i. hydrogen for 2-3 h. The resulting mixture was filtered through Celite and the filtrate concentrated under reduced pressure. Silica gel column chromatography using combinations of hexane-ethyl acetate (typically 3:1 hexane-ethyl acetate) afforded 7-chloro-5-ethyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.051 g, 63%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.28 (t, 3H), 2.74 (q, 2H), 4.23 (s, 2H), 4.81 (s, 2H), 7.12-7.39 (m, 6H). GC-MS: m/z 369 (M)+, 300 (M−69)+.

Workup

  1. filtrationThe resulting mixture was filtered through Celite
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-9fcbfac3d8cd47ae96d191f2867abd81
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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