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

HRID 1723198Notes

Reaction equation

HRID 1723198 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-d9fd5f44364e45d2bbbfda9887546b1a
Source dataset
uspto-grants-1989_08
Patent number
US04859692

Reaction notes

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