HCID 22676723, compound → HCID 22676739, compound

HRID 1006253Notes

Reaction equation

HRID 1006253 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25]CC4C=CC=CC=4)[CH:20]=3)[C:10]=2[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:5][CH:4]=1>[Pd].C(OCC)(=O)C>[OH:25][C:21]1[CH:20]=[C:19]([CH2:18][N:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)=[C:10]2[C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 1

HCID 22676723HCID 22676723, compound

Product 1

HCID 22676739HCID 22676739, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a Parr shaker bottle purged with Argon was added palladium on carbon (Degussa type) (500 mg), ethyl acetate (10 mL), ethyl 3-(4-methoxyphenyl)-1-{[3-(phenylmethoxy)phenyl]methyl}indole-2-carboxylate (Example 45, 5 g crude material, 7.0 mmol, in 120 mL methanol and 40 mL ethyl acetate). The mixture was hydrogenated at 55 psi for 48 h. The mixture was then filtered through Celite and the filtrate was concentrated in vacuo. The residue was purified with silica gel flash chromatography using hexane/ethyl acetate (3/1 to 2/1) to give ethyl 1-[(3-hydroxyphenyl)methyl]-3-(4-methoxyphenyl)indole-2-carboxylate as a light yellow oil (2.5 g, 89%): MS (M+) calcd for C25H23NO4 401.1, found 401.0; 1H NMR (CDCl3) δ 7.60 (dd, J=8.1 Hz, 1H), 7.30-7.45 (m, 4H), 7.13-7.21 (m, 2H), 6.98 (d, J=8.1 Hz, 2H), 6.64-6.78 (m, 2H), 6.52 (s, 1H), 5.77 (s, 2H), 4.14 (q, J=7.0 Hz, 2H), 1.04 (t, J=7.0 Hz, 3H).

Workup

  1. customTo a Parr shaker bottle purged with Argon
  2. filtrationThe mixture was then filtered through Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified with silica gel flash chromatography

Sources & evidence

ORD record
ord-c3e0f1460b714951911a7b56421dceaf
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

Loading…