HCID 22718719, compound → HCID 22718746, compound

HRID 1582641Notes

Reaction equation

HRID 1582641 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=2)[C:7]2[C:12]([CH:13]=1)=[C:11]([F:14])[C:10]([O:15]CC1C=CC=CC=1)=[CH:9][CH:8]=2)=[O:4]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=2)[C:7]2[C:12]([CH:13]=1)=[C:11]([F:14])[C:10]([OH:15])=[CH:9][CH:8]=2)=[O:4]

Participants

4

Reactant 1

HCID 22718719HCID 22718719, compound

Product 1

HCID 22718746HCID 22718746, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl-N-(3,4-dichlorobenzyl)-4-fluoro-5-benzyloxyindole-2-carboxylate (8.22 g) and 5% Pd/C (200 mg) in ethyl acetate (250 ml) was stirred under a hydrogen atmosphere overnight, filtered through celite, concentrated in vacuo and purified by flash column chromatography using a gradient of 0-50% ethyl acetate/iso-hexane as eluent to give the product as a brown solid (6.18 g) 1H NMR (DMSO-d6) δ3.80(s, 3H), 5.75(s, 2H), 6.85(m, 1H), 7.00(t, 1H), 7.22(m, 2H), 7.30(m, 1H), 7.50(m,1H), 9.33(s, 1H); M/z(−) 366.2 (MH−)

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated in vacuo
  3. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-0de8d21058cf4e47aee3076989295261
Source dataset
uspto-grants-2004_05
Patent number
US06737435B1

Reaction notes

Loading…