HCID 60155788, compound → HCID 71278747, compound

HRID 1749760Notes

Reaction equation

HRID 1749760 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2\[O:12][C:13]3[C:20]([CH2:21][N:22]4[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]4)=[C:19]([OH:35])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1.[H][H]>C(O)C.[Pd]>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]2[C:15](=[O:16])[C:14]3[CH:17]=[CH:18][C:19]([OH:35])=[C:20]([CH2:21][N:22]4[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[CH2:24][CH2:23]4)[C:13]=3[O:12]2)=[CH:2]1

Participants

5

Reactant 2

HCID 60155788HCID 60155788, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 71278747HCID 71278747, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of tert-butyl (Z)-4-({2-[(1H-indol-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.030 g, 0.063 mmol) obtained in Example A11, Step 1 in ethanol (2.0 mL) was added with 5% palladium/carbon (wetted with 50% water, 0.027 g) under an argon atmosphere, and then the inside of the reaction vessel was replaced with hydrogen. The reaction mixture was stirred at room temperature for 4 hours, and then filtered through Celite, and the solvent was evaporated under reduced pressure to obtain tert-butyl 4-({2-[(1H-indol-3-yl)methyl]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.028 g, 93%).

Workup

  1. filtrationfiltered through Celite
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c46de5d7df634593884c3e340c497067
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

Loading…