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

HRID 24048Notes

Reaction equation

HRID 24048 reaction equation
C([O:3][C:4](=[O:35])[CH:5]=[C:6]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([CH2:22][CH2:23][CH2:24][C:25]3[CH:34]=[CH:33][C:32]4[C:27](=[N:28][CH:29]=[CH:30][CH:31]=4)[N:26]=3)=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C>CO.[Pd]>[C:7]1([CH:6]([N:13]2[C:21]3[C:16](=[CH:17][C:18]([CH2:22][CH2:23][CH2:24][C:25]4[CH:34]=[CH:33][C:32]5[CH2:31][CH2:30][CH2:29][NH:28][C:27]=5[N:26]=4)=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)[CH2:5][C:4]([OH:35])=[O:3])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 668212473-[5-(3-[1,8]Naphthyridin-2-yl-propyl)-indol-1-yl]-3-phenyl-acrylic acid ethyl ester

Product 1

HCID 101604113-Phenyl-3-{5-[3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-propyl]-indol-1-yl}-propionic acidYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-[5-(3-[1,8]Naphthyridin-2-yl-propyl)-indol-1-yl]-3-phenyl-acrylic acid ethyl ester (30.0 mg, 0.484 mmol) in methanol (2 mL) was stirred under hydrogen in the presence of 10% palladium on carbon (15.0 mg) at room temperature for 3 days. Then, the reaction mixture was filtered through celite and purified via column chromatography on silica gel (methylene chloride/methanol) (95/5) to give the title product as yellow oil (20.0 mg, 66% yield). 1H NMR (CDCl3) δ 8.2 (d, 1H), 8.0 (m, 1H), 7.45 (m, 2H), 7.27 (m, 2H), 6.9-7.2 (m, 4H), 6.5 (1H), 6.3 (1H), 6.20 (m, 1H), 6.10 (m, 1H), 4.15 (m, 2H), 3.4 (m, 2H), 3.3 (m, 4H), 2.6 (m, 4H), 2.1 (m, 2H), 1.89 (m, 2H). Mass Spectrum (LCMS, ESI) calculated for C30H34N3O2 468.27 (M+H); found 468.3.

Workup

  1. filtrationThen, the reaction mixture was filtered through celite
  2. custompurified via column chromatography on silica gel (methylene chloride/methanol) (95/5)

Sources & evidence

ORD record
ord-68c7440a6845460f91f490e79b1255c7
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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