HCID 86752486, compound → HCID 18926518, compound

HRID 1600183Notes

Reaction equation

HRID 1600183 reaction equation
[N:1]1([CH2:6][C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13](/[CH:16]=[CH:17]/[C:18]([O:20]CC4C=CC=CC=4)=[O:19])[CH:14]=3)[N:9]([CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])[C:8]=2[CH3:34])[CH:5]=[CH:4][N:3]=[CH:2]1>O1CCCC1.[Pd]>[C:18]([CH2:17][CH2:16][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])[C:8]([CH3:34])=[C:7]2[CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)([OH:20])=[O:19]

Participants

4

Reactant 1

HCID 86752486HCID 86752486, compound

Product 1

HCID 18926518HCID 18926518, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl (E)-3-[3-(1H-imidazol-1-ylmethyl)-1-(2-methoxycarbonylethyl)-2-methyl-1H-indol-5-yl]-2-propenoate (2.0 g) in tetrahydrofuran (40 ml) was hydrogenatedat room temperature and 4.5 atm. in the presence of 10% palladium on carbon(0.20 g) until reaction was complete (5 hours). The mixture was filtered and the residue was washed with ethyl acetate. The combined filtrate and washings were evaporated and the residue was triturated with ether to givethe title compound (1.52 g), m.p. 134°-137° C. Found: C,65.31; H,6.35; N,10.70. C20H23N3O4 requires: C,65.02; H,6.28N,11.38%.

Workup

  1. customwas hydrogenatedat room temperature
  2. custom(5 hours)
  3. filtrationThe mixture was filtered
  4. washthe residue was washed with ethyl acetate
  5. customThe combined filtrate and washings were evaporated
  6. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-c959a83398204dfbb35d8c0348a654ba
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

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