Tetrabutylammonium Fluoride → 2-[3-(1H-indol-5-yl)-propyl]-[1,8]naphthyridine

HRID 24042Notes

Reaction equation

HRID 24042 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([Si](C(C)C)(C(C)C)[N:23]1[C:31]2[C:26](=[CH:27][C:28]([CH2:32][CH2:33][CH2:34][C:35]3[CH:44]=[CH:43][C:42]4[C:37](=[N:38][CH:39]=[CH:40][CH:41]=4)[N:36]=3)=[CH:29][CH:30]=2)[CH:25]=[CH:24]1)(C)C>C1COCC1>[NH:23]1[C:31]2[C:26](=[CH:27][C:28]([CH2:32][CH2:33][CH2:34][C:35]3[CH:44]=[CH:43][C:42]4[C:37](=[N:38][CH:39]=[CH:40][CH:41]=4)[N:36]=3)=[CH:29][CH:30]=2)[CH:25]=[CH:24]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 225702802-[3-(1-triisopropylsilanyl-1H-indol-5-yl)-propyl]-[1,8]naphthyridine

Product 1

HCID 225702772-[3-(1H-indol-5-yl)-propyl]-[1,8]naphthyridineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride [1.0 M in THF] (5.10 mL, 5.10 mmol) was added to a solution of 2-[3-(1-triisopropylsilanyl-1H-indol-5-yl)-propyl]-[1,8]naphthyridine (1.14 g, 2.57 mmol) in THF (20 mL) at room temperature and stirred for 1 h. The solvent was removed and the resulting crude product was purified via column chromatography on silica gel, eluting with ethyl acetate/hexane (2/1) to give the title product (100% yield). 1H NMR (CDCl3) δ 9.08 (dd, J=2.0, 4.3 Hz, 1H), 8.28 (br, 1H), 8.14 (dd, J=2.0, 8.1, 1H), 8.07 (d, J=8.4 Hz, 1H), 7.45 (m, 2H), 7.36 (d, J=8.3, 1H), 731 (d, J=8.3 Hz, 1H), 7.18 (t, J=2.8 Hz, 1H), 7.05 (dd, J=1.6, 8.3 Hz, 1H), 6.47 (m, 1H), 3.10 (t, J=7.8 Hz, 2H), 2.84 (t, J=7.7 Hz, 2H), 2.28 (m, 2H). Mass Spectrum (LCMS, ESI) calculated for C19H18N3 288.2 (M+H); found 288.2.

Workup

  1. customThe solvent was removed
  2. customthe resulting crude product was purified via column chromatography on silica gel
  3. washeluting with ethyl acetate/hexane (2/1)

Sources & evidence

ORD record
ord-808dbecc85bb4d83bfa7c54afec35e4e
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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