Triphenylphosphine → 3-(5-{2-[6-(Methylamino)-2-pyridyl]ethoxy}indolyl)propanoic acid

HRID 23977Notes

Reaction equation

HRID 23977 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH3:15][NH:16][C:17]1[N:22]=[C:21]([CH2:23][CH2:24][OH:25])[CH:20]=[CH:19][CH:18]=1.O[C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][C:31]([CH2:36][CH2:37][C:38]([O:40]C)=[O:39])=[CH:30]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:15][NH:16][C:17]1[N:22]=[C:21]([CH2:23][CH2:24][O:25][C:27]2[CH:28]=[C:29]3[C:33](=[CH:34][CH:35]=2)[NH:32][C:31]([CH2:36][CH2:37][C:38]([OH:40])=[O:39])=[CH:30]3)[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 105348582-[6-(Methylamino)-2-pyridyl]ethan-1-olHCID 22570384methyl 3-(5-hydroxy-1H-indol-2-yl)propanoate

Product 1

HCID 225702733-(5-{2-[6-(Methylamino)-2-pyridyl]ethoxy}indolyl)propanoic acidYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (0.19 g, 0.94 mmol) was added to a solution of 2-[6-(methylamino)-2-pyridyl]ethan-1-ol (0.10 g, 0.66 mmol), as prepared in step e of Example 5, methyl 3-(5-hydroxyindolyl)propanoate (0.10 g, 0.46 mmol), as prepared in the preceding step, and triphenylphosphine (0.24 g, 0.92 mmol) in tetrahydrofuran (5.0 mL) at 0° C. in an ice bath. After stirring at ambient temperature overnight (16 h), the reaction was concentrated and the residue was purified by flash chromatography on silica gel (20%-30% ethyl acetate in hexane) to give the title compound as a yellow oil (0.023 g, 15%). 1H-NMR (400 M Hz, CDCl3) δ 7.39 (t, J=7.3 Hz, 1H), 7.20 (d, J=8.9 Hz, 1H), 7.11 (d, J=2.3 Hz, 1H), 7.07 (d, J=3.1 Hz, 1H ), 6.87 (dd, J=2.4, 8.9 Hz, 1H), 6.56 (d, J=7.2 Hz, 1H), 6.37 (d, J=3.1 Hz, 1H), 6.24 (d, J=8.2 Hz, 1H), 4.56 (br s, 1H), 3.40 (t, J=6.9 Hz, 2H), 4.34 (t, J=7.0 Hz, 2H), 3.65 (s, 3H), 3.10 (t, J=7.0 Hz, 2H), 2.89 (d, J=4.8 Hz, 2H), 2.80 (t, J=6.9 Hz, 2H).

Workup

  1. concentrationthe reaction was concentrated
  2. customthe residue was purified by flash chromatography on silica gel (20%-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-3c83338487c04c578d9ede1d5a89bb7a
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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