HCID 66992743, compound → HCID 66992953, compound

HRID 1855672Notes

Reaction equation

HRID 1855672 reaction equation
[C:1]([N:20]1[CH:24]=[C:23]([CH:25]=[CH:26][CH2:27][CH2:28][CH2:29][N:30]2[C:38](=[O:39])[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]2=[O:40])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].CO.C1COCC1>[C:1]([N:20]1[CH:24]=[C:23]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][N:30]2[C:38](=[O:39])[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]2=[O:40])[N:22]=[CH:21]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 66992743HCID 66992743, compound

Product 1

HCID 66992953HCID 66992953, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

785 mg (1.5 mmol) of 2-[5-(1-trityl-1H-imidazol-4-yl)pent-4-enyl]isoindole-1,3-dione, 10 ml of a MeOH/THF mixture (6/4) and 392 mg of 10% Pd/C are introduced into a Parr bomb. The reaction medium is stirred at room temperature under a hydrogen pressure of 5 bar. After 4 hours, the reaction medium is filtered through Celite and concentrated. The crude product obtained is chromatographed on silica gel (eluent: heptane/EtOAc (5/5) and then CH2Cl2/MeOH (9/1)). 380 mg of 2-[5-(1-trityl-1H-imidazol-4-yl)pentyl]isoindole-1,3-dione in the form of a white powder are obtained in a yield of 48%.

Workup

  1. filtrationthe reaction medium is filtered through Celite
  2. concentrationconcentrated
  3. customThe crude product obtained
  4. customis chromatographed on silica gel (eluent

Sources & evidence

ORD record
ord-2dd0ee38863c46439900e4ab163c2e49
Source dataset
uspto-grants-2015_02
Patent number
US08962846B2

Reaction notes

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