3-{5-[2-(2-Methyl-[1,8]naphthyridin-3-yl)-ethyl]-indol-1-yl}-acrylic acid methyl ester → 3-{5-[2-(2-Methyl-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-ethyl]-indol-1-yl}-propionic acid methyl ester

HRID 24041Notes

Reaction equation

HRID 24041 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH:4]=[CH:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([CH2:15][CH2:16][C:17]3[C:18]([CH3:27])=[N:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][N:21]=4)=[CH:12][CH:13]=2)[CH:8]=[CH:7]1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([CH2:15][CH2:16][C:17]3[C:18]([CH3:27])=[N:19][C:20]4[NH:21][CH2:22][CH2:23][CH2:24][C:25]=4[CH:26]=3)=[CH:12][CH:13]=2)[CH:8]=[CH:7]1

Participants

4

Reactant 1

HCID 668213693-{5-[2-(2-Methyl-[1,8]naphthyridin-3-yl)-ethyl]-indol-1-yl}-acrylic acid methyl ester

Product 1

HCID 668214593-{5-[2-(2-Methyl-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-ethyl]-indol-1-yl}-propionic acid methyl esterYield 6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-{5-[2-(2-Methyl-[1,8]naphthyridin-3-yl)-ethyl]-indol-1-yl}-acrylic acid methyl ester (230 mg, 6.1 mmol) was stirred in methanol (5 mL) under a hydrogen atmosphere in the presence of 10% palladium on carbon (10% w/w) (20 mg) for 3 days. After removal of solvent, the crude product was purified by flash chromatography on silica gel with methylene chloride/methanol (95/5) to give the title product (14 mg, 6% yield). 1H NMR (CDCl3) δ 7.40 (1H), 7.33 (1H), 7.23 (1H), 7.10 (1H), 7.00 (d, 1H), 6.65 (br, 1H), 6.45 (1H), 4.45 (t, 2H), 3.67 (s, 3H), 3.40 (br, 2H), 2.85 (4H), 2.30 (s, 3H), 2.70 (m, 2H), 1.90 (m, 2H). Mass Spectrum (LCMS, ESI) calculated for C23H28N3O2 378.2 (M+H); found 378.3.

Workup

  1. customAfter removal of solvent
  2. customthe crude product was purified by flash chromatography on silica gel with methylene chloride/methanol (95/5)

Sources & evidence

ORD record
ord-946a01c776db4ed3a9bf3d3af040e141
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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