HCID 15063396, compound → HCID 15063397, compound

HRID 475476Notes

Reaction equation

HRID 475476 reaction equation
[C:1]([O:5][C:6](=[O:24])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([O:5][C:6](=[O:24])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 15063396HCID 15063396, compound

Product 1

HCID 15063397HCID 15063397, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To the ethyl (2E)-3-[1-(2-tert-butoxy-2-oxoethyl)-1H-indol-2-yl] acrylate from Step 3 in EtOAc (0.08 M) was added 10% palladium on carbon (50 mg per g of substrate). The reaction mixture was flushed a few times with hydrogen and then stirred overnight at rt under a 1 atmosphere pressure of hydrogen. The reaction mixture was diluted with CH2Cl2 (2 mL/g) and was filtered through Celite. The filtrate was concentrated to dryness to afford the title compound crude (100%) which was used in the next step without further purification.

Workup

  1. customThe reaction mixture was flushed a few times with hydrogen
  2. additionThe reaction mixture was diluted with CH2Cl2 (2 mL/g)
  3. filtrationwas filtered through Celite
  4. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-3cfec4c44a054677817d134b7b033d8b
Source dataset
uspto-grants-2014_01
Patent number
US08637541B2

Reaction notes

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