HCID 57949551, compound → HCID 57949541, compound

HRID 2427774Notes

Reaction equation

HRID 2427774 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:22]=[N:23][N:24]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[CH:25]=2)[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]#[C:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:7]2>CCO.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:22]=[N:23][N:24]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[CH:25]=2)[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:7]2

Participants

4

Reactant 1

HCID 57949551HCID 57949551, compound

Product 1

HCID 57949541HCID 57949541, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 7-chloro-2-(3-phenylprop-2-ynyl)-5-(1-pyridin-2-ylmethyl-1H-pyrazol-4-yl)-2,3-dihydroisoindol-1-one (30 mg, 0.07 mmol) in EtOH (5 mL) was added 10% Pd on carbon (16.5 mg). A H2 balloon was attached to the flask. After 16 hours the reaction was filtered and concentrated to provide the title compound (29.7 mg, 98%) as a yellow oil. 1H NMR (300 MHz, CDCl3): δ (ppm) 8.61 (ddpg, 1H), 7.88 (m, 2H), 7.70 (t, 1H), 7.48 (d, 2H), 7.40 (d, 2H), 7.23 (m, 8H), 5.49 (s, 2H), 4.32 (s, 2H), 3.68 (t, 2H), 2.70 (t, 2H), 2.00 (tt, 2H).

Workup

  1. filtrationAfter 16 hours the reaction was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-0adb13c268e84a8f9b5a5a9125b0d9ea
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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