3-(2-Methoxy-4-methoxycarboxybenzyl)-5-nitroindole → Methyl 4-(5-aminoindol-3-ylmethyl)-3-methoxybenzoate

HRID 1742296Notes

Reaction equation

HRID 1742296 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)[NH:16][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)[NH:16][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 114732633-(2-Methoxy-4-methoxycarboxybenzyl)-5-nitroindole

Product 1

HCID 23365920Methyl 4-(5-aminoindol-3-ylmethyl)-3-methoxybenzoateYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Palladium-on-carbon (10% w/w; 0.25 g.) was added to a solution of (C) (1.5 g.) in tetrahydrofuran (50 ml.) in a hydrogenation bottle. The mixture was hydrogenated at 3.45 bars 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 on silica gel (200 ml.) eluting with 1:1 v/v ethyl acetate:hexane, to give methyl 4-(5-aminoindol-3-ylmethyl)-3-methoxybenzoate (A) (1.12 g., 82%) as a viscous oil; NMR: 3.29(br,2H,NH2), 3.88(s,3H, CO.OCH3), 3.91(s,3H, OCH3), 4.03(s,2H, CH2.Ar), 6.64(dd,1H), 6.78(m,2H), 7.10(m,2H), 7.44(m,2H), 7.68(br,1H, H1 -indole).

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 on silica gel (200 ml.)
  4. washeluting with 1:1 v/v ethyl acetate

Sources & evidence

ORD record
ord-d8ee8d0400ca4d7b8fc2a2b3b784c001
Source dataset
uspto-grants-1994_08
Patent number
US05338734

Reaction notes

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