5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1-(4-nitrobenzyl)-1H-indole-2-carboxylic acid ethyl ester → 1-(4-Amino-benzyl)-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1H-indole-2-carboxylic Acid Ethyl Ester

HRID 342806Notes

Reaction equation

HRID 342806 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH2:15][C:16]1([CH3:21])[O:20][CH2:19][CH2:18][O:17]1)=[CH:10][CH:9]=2)=[O:5])[CH3:2].[H][H]>O1CCCC1.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([NH2:29])=[CH:27][CH:28]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH2:15][C:16]1([CH3:21])[O:20][CH2:19][CH2:18][O:17]1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 675989085-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1-(4-nitrobenzyl)-1H-indole-2-carboxylic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 675989771-(4-Amino-benzyl)-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1H-indole-2-carboxylic Acid Ethyl EsterYield 102.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of crude 5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1-(4-nitrobenzyl)-1H-indole-2-carboxylic acid ethyl ester (2.4 g, ≈5 mmol) in dry tetrahydrofuran (20 ml) was shaken in a Parr apparatus with 10% palladium on carbon (200 mg) under 40 psi hydrogen for about four hours. The mixture was filtered and evaporated under reduced pressure to give the title compound (2.03 g), which was reacted without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-94e94ed866c54f588ad14e26d3c0a426
Source dataset
uspto-grants-1999_01
Patent number
US05859044

Reaction notes

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