3-[5-(3-[1,8]Naphthyridin-2-yl-propyl)-indol-1-yl]-hexanoic acid ethyl ester → 3-{5-[3-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)-propyl]-indol-1-yl}-hexanoic acid ethyl ester

HRID 24045Notes

Reaction equation

HRID 24045 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH2:5][CH:6]([N:10]1[C:18]2[C:13](=[CH:14][C:15]([CH2:19][CH2:20][CH2:21][C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[N:25][CH:26]=[CH:27][CH:28]=4)[N:23]=3)=[CH:16][CH:17]=2)[CH:12]=[CH:11]1)[CH2:7][CH2:8][CH3:9])[CH3:2]>[Pd].CO>[CH2:1]([O:3][C:4](=[O:32])[CH2:5][CH:6]([N:10]1[C:18]2[C:13](=[CH:14][C:15]([CH2:19][CH2:20][CH2:21][C:22]3[CH:31]=[CH:30][C:29]4[CH2:28][CH2:27][CH2:26][NH:25][C:24]=4[N:23]=3)=[CH:16][CH:17]=2)[CH:12]=[CH:11]1)[CH2:7][CH2:8][CH3:9])[CH3:2]

Participants

4

Reactant 1

HCID 668213643-[5-(3-[1,8]Naphthyridin-2-yl-propyl)-indol-1-yl]-hexanoic acid ethyl ester

Product 1

HCID 668215293-{5-[3-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)-propyl]-indol-1-yl}-hexanoic acid ethyl esterYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-[5-(3-[1,8]naphthyridin-2-yl-propyl)-indol-1-yl]-hexanoic acid ethyl ester (100 mg, 0.665 mmol) and 10% palladium on carbon (30 mg) in methanol (5 mL) was stirred under hydrogen for 2 days. The reaction solution was filtered through celite and dried to give the crude product, which was purified via column chromatography eluting with hexane/ethyl acetate (4/1), to give the title compound (80% yield). 1H NMR (CDCl3) δ 7.39 (d, J=0.9 Hz, 1H), 7.31 (d, J=8.5 Hz, 1H), 7.02-7.10 (m, 3H), 6.44 (dd, J=3.6, 6.3 Hz, 1H), 6.33 (d, J=7.3 Hz, 1H), 5.60 (br, 1H), 4.82 (m, 1H), 3.97 (q, 2H), 3.35 (t, 2H), 2.60-2.80 (m, 8H), 1.80-2.10 (m, 6H), 1.20 (m, 2H), 1.11 (m, 3H), 0.87 (m, 3H). Mass Spectrum (LCMS, ESI) calculated for C27H36N3O2 434.3 (M+H); found 434.4.

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. customdried
  3. customto give the crude product, which
  4. customwas purified via column chromatography
  5. washeluting with hexane/ethyl acetate (4/1)

Sources & evidence

ORD record
ord-0d8675a4ae19402492d45244fd987d78
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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