HCID 22718742, compound → HCID 22718724, compound

HRID 1582642Notes

Reaction equation

HRID 1582642 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[C:8]2[C:13]([C:14]=1[O:15][CH3:16])=[CH:12][C:11]([O:17]CC1C=CC=CC=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[C:8]2[C:13]([C:14]=1[O:15][CH3:16])=[CH:12][C:11]([OH:17])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 22718742HCID 22718742, compound

Product 1

HCID 22718724HCID 22718724, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5% Pd/C (100 mg) was added to a stirred solution of ethyl-N-(3,4-dichlorobenzyl)3-methoxy-5-benzyloxyindole-2-carboxylate (0.9 g) in ethyl acetate (50 ml) and the mixture was hydrogenated for 12 hours. Catalyst filtered off and filtrate evaporated to give a brown oil (0.61 g) which was used without further purification. NMR: δ 1.4 (t, 3H), 4.0 (s, 3H), 4.4 (q, 2H), 5.6 (s, 2H), 6.8 (dd, 1H), 6.9 (dd, 1H), 7.1 (m, 3H), 7.3 (d,1H); m/z 394 (MH+)

Workup

  1. filtrationCatalyst filtered off
  2. customfiltrate evaporated

Sources & evidence

ORD record
ord-33ca54bdc17d4c83929bc737c0ee654d
Source dataset
uspto-grants-2004_05
Patent number
US06737435B1

Reaction notes

Loading…