Methyl 3-methoxy-4-(1-ethyl-5-nitroindol-3-ylmethyl)benzoate → HCID 23365902, compound

HRID 1904466Notes

Reaction equation

HRID 1904466 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([N+:23]([O-])=O)[CH:21]=2)[N:16]([CH2:26][CH3:27])[CH:15]=1)[C:6]([O:8][CH3:9])=[O:7]>O1CCCC1.[Pd]>[NH2:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:26][CH3:27])[CH:15]=[C:14]2[CH2:13][C:12]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 1

HCID 20038743Methyl 3-methoxy-4-(1-ethyl-5-nitroindol-3-ylmethyl)benzoate

Product 1

HCID 23365902HCID 23365902, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ester (G) (4.80 g) in tetrahydrofuran (75 ml) was hydrogenated in the presence of palladium-on-carbon (10% w/w; 0.25 g), at 3.45 bar for 2 hours. The catalyst was removed by filtration through diatomaceous earth and the filtrate was evaporated. The residual oil was purified by flash chromatography to give methyl 4-(5-amino-1-ethylindol-3-ylmethyl)-3-methoxybenzoate (H) as an amber oil (4.43 g, 100%); TLC, silica gel, Rf =0.23, hexane:ethyl acetate (6:4 v/v).

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. customthe filtrate was evaporated
  3. customThe residual oil was purified by flash chromatography

Sources & evidence

ORD record
ord-bb69b55ea8b342adaaf122ab7b4257a1
Source dataset
uspto-grants-1989_06
Patent number
US04837235

Reaction notes

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