HCID 66765143, compound → HCID 56837596, compound

HRID 1466788Notes

Reaction equation

HRID 1466788 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[C:10]([S:18][C:19]2[CH:20]=[C:21](/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28])[CH:22]=[CH:23][CH:24]=2)=[C:9]1[CH3:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.CO.[Pd]>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[C:10]([S:18][C:19]2[CH:20]=[C:21]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])[CH:22]=[CH:23][CH:24]=2)=[C:9]1[CH3:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 66765143HCID 66765143, compound

Product 1

HCID 56837596HCID 56837596, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

(E)-3-[3-(1-Benzyl-6-chloro-2-methyl-1H-indol-3-ylsulfanyl)-phenyl]-acrylic acid (0.2912 g, 0.67 mmol) was dissolved in EtOAc:MeOH (7:3, 10 mL) then palladium on carbon (0.214 g, 10% by weight, wet 50% H2O) was added and H2 (g) was bubbled through the mixture for 5 minutes. The reaction was stirred overnight under H2 atmosphere and then the palladium on carbon was filtered off. Standard workup procedure followed by preparatory HPLC (10-100% ACN in H2O) provided the title compound.

Workup

  1. customH2 (g) was bubbled through the mixture for 5 minutes
  2. filtrationthe palladium on carbon was filtered off

Sources & evidence

ORD record
ord-806f1d33a33b4b589de479c238f49db0
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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