Ethyl 3-(5-(oct-1-ynyl)indoline-1-carboxamido)propanoate → HCID 66614892, compound

HRID 717640Notes

Reaction equation

HRID 717640 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]([NH:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:19])[CH2:13][CH2:12]2)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>CCO.[Pd]>[CH2:1]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]([NH:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:19])[CH2:13][CH2:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 1

HCID 66615094Ethyl 3-(5-(oct-1-ynyl)indoline-1-carboxamido)propanoate

Product 1

HCID 66614892HCID 66614892, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the product of Step C (0.1 g; 0.27 mmol) and 10% Pd/C (0.1 g) in EtOH (15 ml) was stirred at room temperature for 1 h under H2 (balloon). The catalyst was removed by filtration through the Celite pad, washed with CH2Cl2 (2×10 ml) and combined filtrates were evaporated to dryness under reduced pressure to give a title compound (0.09 g; 90%), as colourless solid. 1H-NMR (CDCl3) 7.71 (d, 1H, J=8.8 Hz); 6.94 (d, 1H, J=8.8 Hz); 6.93 (s, 1H); 5.29 (m, 1H); 4.14 (q, 2H, J=7 Hz); 3.82 (t, 2H, J=8.8 Hz); 3.57 (q, 2H, J=5.9 Hz); 3.11 (t, 2H, J=8.6 Hz); 2.59 (t, 2H, J=5.7 Hz); 2.51 (t, 2H, J=7.7 Hz); 1.57 (m, 2H); 1.26 (m, 13H); 0.86 (t, 3H, J=7 Hz).

Workup

  1. customThe catalyst was removed by filtration through the Celite pad
  2. washwashed with CH2Cl2 (2×10 ml)
  3. customwere evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-5afdf111d5304ae29cba8b3a9679c037
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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