HCID 66917857, compound → HCID 21950008, compound

HRID 2215808Notes

Reaction equation

HRID 2215808 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH:10]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:3]=[CH:2]1>[Pd].C1COCC1.CO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:3]=[CH:2]1

Participants

4

Reactant 1

HCID 66917857HCID 66917857, compound

Product 1

HCID 21950008HCID 21950008, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of ethyl 3-(indol-7-yl)acrylate (13.0 g, 60.5 mmol) in 1:1 THF/MeOH (120 mL), was added to a Parr bottle containing 10% Pd/C (0.87 g, 0.83 mmol). The mixture was hydrogenated in a Parr shaker over 3 h. The mixture was filtered over Celite and concentrated to afford the title compound (12.8 g, 97%) as a white solid. 1H NMR (400 MHz, DMSO-d6) 11.09 (s, 1H), 7.36 (dd, J=6, 2.4 Hz, 1H), 7.29 (t, J=2.4 Hz, 1H), 6.86–6.90 (m, 2H), 6.40 (dd, J=2.8, 2.0 Hz, 1H), 4.04 (q, J=6.8 Hz, 2H), 3.09 (t, J=7.2 Hz, 2H), 2.68 (t, J=7.2 Hz, 2H), 1.13 (t, J=6.8 Hz, 3H). MS (electrospray, m/z) 218.1 (M++1).

Workup

  1. filtrationThe mixture was filtered over Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-5b54e2db82e54cf5be810578618ef900
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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