HCID 23365875, compound → HCID 23365881, compound

HRID 275162Notes

Reaction equation

HRID 275162 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:13]([O-])=O)=[CH:10][CH:11]=2)[C:6]([CH2:16][C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][C:18]=2[O:26][CH3:27])=[CH:5]1)(=[O:3])[CH3:2]>[Pd].CO>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([NH2:13])=[CH:10][CH:11]=2)[C:6]([CH2:16][C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][C:18]=2[O:26][CH3:27])=[CH:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 23365875HCID 23365875, compound

Product 1

HCID 23365881HCID 23365881, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium-on-carbon (10% w/w, 0.1 g.) was added to a solution of 4-(1-acetyl-5-nitroindol-3-ylmethyl)-3-methoxybenzoic acid (0.35 g.) in a mixture of 1:1 v/v methanol:tetrahydrofuran (50 ml.), which solution had been deoxygenated by passing a stream of nitrogen gas through it, and the mixture hydrogenated at an initial pressure of 50 psi. After 24 hours, the catalyst was removed by filtration through diatomaceous earth, and the filtrate evaporated to give 4-(1-acetyl-5-aminoindol-3-ylmethyl)-3-methoxybenzoic acid (Z) (0.31 g., 91%); partial NMR (250 MHz, CD3OD): 2.53(s,3H, NCOCH3); 3.94(s,3H, OMe); 4.00(s,2H, ArCH2).

Workup

  1. customtetrahydrofuran (50 ml.), which solution had been deoxygenated
  2. customthe catalyst was removed by filtration through diatomaceous earth
  3. customthe filtrate evaporated

Sources & evidence

ORD record
ord-9cbdd52a59984274a31b9842c957899d
Source dataset
uspto-grants-1995_02
Patent number
US05391758

Reaction notes

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