Sodium hydride → 3-[5-(3-[1,8]Naphthyridin-2-yl-propyl)-indol-1-yl]-hexanoic acid ethyl ester

HRID 24044

Reaktionsgleichung

Reaktionsgleichung von HRID 24044
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][CH2:11][CH2:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[N:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH2:25]([O:27][C:28](=[O:35])[CH2:29][CH:30](Br)[CH2:31][CH2:32][CH3:33])[CH3:26]>CN(C=O)C>[CH2:25]([O:27][C:28](=[O:35])[CH2:29][CH:30]([N:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][CH2:11][CH2:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[N:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[CH2:31][CH2:32][CH3:33])[CH3:26]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 225702772-[3-(1H-indol-5-yl)-propyl]-[1,8]naphthyridineHCID 22570372Ethyl-beta-bromocaproate

Produkt 1

HCID 668213643-[5-(3-[1,8]Naphthyridin-2-yl-propyl)-indol-1-yl]-hexanoic acid ethyl esterAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-[3-(1H-indol-5-yl)-propyl]-[1,8]naphthyridine (0.18 g, 0.62 mmol) in DMF (2 mL) was added sodium hydride (30.0 mg, 1.24 mmol) at room temperature. After stirring for 15 minutes, 3-bromo-hexanoic acid ethyl ester (276 mg, 1.24 mmol) was added. The reaction mixture was stirred overnight and quenched with water. The crude product was extracted with methylene chloride, washed with brine, and purified via column chromatography with silica gel (ethyl acetate/hexane:1:1), to give the title product (17% yield). 1H NMR (CDCl3) δ 9.08 (dd, J=1.7, 4.0 Hz, 1H), 8.14 (m, 1H), 8.06 (m, 1H), 7.32-7.44 (m, 4H), 7.05-7.12 (m, 2H), 6.45 (d, J=3.2 Hz, 1H), 4.81 (m, 1H), 3.99 (m, 2H), 3.08 (m, 2H), 2.83 (m, 4H), 2.22 (m, 2H), 1.90 (m, 2H), 1.20 (m, 2H), 1.07 (m, 3H), 0.87 (m, 3H). Mass Spectrum (LCMS, ESI) calculated for C27H32N3O2 430.3 (M+H); found 430.3.

Aufarbeitung

  1. stirringThe reaction mixture was stirred overnight
  2. customquenched with water
  3. extractionThe crude product was extracted with methylene chloride
  4. washwashed with brine
  5. custompurified via column chromatography with silica gel (ethyl acetate/hexane:1:1)

Quellen und Nachweise

ORD-Eintrag
ord-301af04e9db84a50b66dc225119971a0
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855722B2

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