Triphenylphosphine → 7-{2-[1-(1-Ethoxycarbonylmethyl-butyl)-1H-indol-5-yloxy]-ethyl}-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester

HRID 1295137Notes

Reaction equation

HRID 1295137 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([O:24][C:25]([N:27]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([CH2:37][CH2:38][OH:39])[N:35]=2)[CH2:30][CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].[CH2:40]([O:42][C:43](=[O:59])[CH2:44][CH:45]([N:49]1[C:57]2[C:52](=[CH:53][C:54](O)=[CH:55][CH:56]=2)[CH:51]=[CH:50]1)[CH2:46][CH2:47][CH3:48])[CH3:41].CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:20]([O:24][C:25]([N:27]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([CH2:37][CH2:38][O:39][C:54]3[CH:53]=[C:52]4[C:57](=[CH:56][CH:55]=3)[N:49]([CH:45]([CH2:44][C:43]([O:42][CH2:40][CH3:41])=[O:59])[CH2:46][CH2:47][CH3:48])[CH:50]=[CH:51]4)[N:35]=2)[CH2:30][CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 58230650tert-Butyl 7-(2-hydroxyethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylateHCID 674263943-(5-Hydroxy-indol-1-yl)-hexanoic acid ethyl ester

Product 1

HCID 668215127-{2-[1-(1-Ethoxycarbonylmethyl-butyl)-1H-indol-5-yloxy]-ethyl}-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl esterYield 13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (0.20 g, 0.77 mmol) was added to a solution of 7-(2-hydroxy-ethyl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (0.16 g, 0.58 mmol) and 3-(5-hydroxy-indol-1-yl)-hexanoic acid ethyl ester (0.10 g, 0.38 mmol) in THF (4 mL) at 0° C. Diisopropylazodicarboxylate (0.15 g, 0.77 mmol) was added dropwise and the reaction was stirred at room temperature overnight. The solution was then concentrated. The residue was purified by flash chromatography on silica gel (30% ethyl acetate in hexane) to give the title compound (13% yield). 1H NMR (CDCl3) δ 7.30 (m, 2H), 7.09 (m, 2H), 6.96 (d, 1H, J=7.6 Hz), 6.86 (m, 1H), 6.41 (d, 1H, J=3.2 Hz), 4.78 (m, 1H), 4.39 (t, 2H, J=6.9 Hz), 3.98 (q, 2H), J=7.1 Hz), 3.75 (m, 2H), 3.21 (t, 2H, J=6.9 Hz), 2.86 (m, 2H), 2.77 (m, 2H), 1.85 (m, 4H), 1.50 (s, 9H), 1.20 (m, 2H), 1.06 (t, 3H, J=7.1 Hz), 0.85 (t, 3H, J=7.4 Hz).

Workup

  1. concentrationThe solution was then concentrated
  2. customThe residue was purified by flash chromatography on silica gel (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-aa72e02d301e4abab24c08c8c0b7abda
Source dataset
uspto-grants-2007_07
Patent number
US07241789B2

Reaction notes

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