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

HRID 23978Notes

Reaction equation

HRID 23978 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([CH2:9][CH2:10][O:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16]([CH2:21][CH2:22][C:23]([O:25]C)=[O:24])=[CH:15]3)[CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>CO.O>[CH3:1][NH:2][C:3]1[N:8]=[C:7]([CH2:9][CH2:10][O:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:15]3)[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22570250Methyl 3-(5-{2-[6-(methylamino)-2-pyridyl]ethoxy}indolyl)propanoate

Product 1

HCID 225702733-(5-{2-[6-(Methylamino)-2-pyridyl]ethoxy}indolyl)propanoic acidYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-(5-{2-[6-(methylamino)-2-pyridyl]ethoxy}indolyl)propanoate (0.023 g, 0.65 mmol), as prepared in the preceding step, in methanol (3 mL) was added sodium hydroxide (0.15 g, 3.8 mmol) in H2O (0.5 mL) and the reaction was stirred for 6 hours at ambient temperature. After evaporating the solvent in vacuo, the residue is taken up in H2O (5 mL) and acidified to pH 4-5 with 10% HCl, extracted with a mixture of ethyl acetate and butanol (2×50 mL) and the combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated to give the title compound as a solid (0.018 g, 82%). 1H-NMR (400 M Hz, CDCl3+CD3OD) δ 7.52 (t, J=7.3 Hz, 1H), 7.25 (d, J=8.9 Hz, 1H), 7.14 (d, J=3.1 Hz, 1H), 7.06 (d, J=2.3 Hz, 1H), 6.81 (dd, J=8.9, 2.4 Hz, 1H), 6.60 (d, J=7.3 Hz, 1H), 6.38 (d, J=8.6 Hz, 1H), 6.33 (d, J=3.2 Hz, 1H), 4.38 (t, J=7.0 Hz, 2H), 4.24 (t, J=6.6 Hz, 2H), 3.06 (t, J=6.6 Hz, 2H), 2.89 (s, 3H), 2.77 (t, J=6.9 Hz, 2H). Mass spectrum (LCMS, ESI pos.) Calcd. for C19H21N3O3 340.3 (M+H); Found: 340.9.

Workup

  1. customAfter evaporating the solvent in vacuo
  2. extractionextracted with a mixture of ethyl acetate and butanol (2×50 mL)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-11eef597eb834f6dab955c48e6fb6004
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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